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Dec 10, 2017 · 24m · top-founders

869 SaaS: Almost 1m Employees Paying $4/mo Use This Time Tracking Software

Nathan Latka · 8m spoken
0:00 / 0:00

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In this episode of The Top Entrepreneurs Podcast, host Nathan Latka interviews T-Sheets co-founder Matt to uncover how the time-tracking SaaS platform scaled to hundreds of thousands of paid seats and an estimated $40 million ARR through disciplined capital management and payroll integration.

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 39% of the talking time here. How this is scored →

Nathan as informed peer 6.0 Guest teaching 3.9 Guest disagreement 2.1 Nathan pushing back 5.0
05100:0010:0020:001:12–3:52 · Nathan as informed peer 6/10 Marketplace Reviews and Viral Employee Referrals Nathan immediately challenges Matt on his marketing claim of being the top-rated time tracking software on the market, demanding specific proof. Matt substantiates the claim using Intuit app store metrics and virality via departing employees, while Nathan calculates the unit economics using his own business as an example.3:53–8:01 · Nathan as informed peer 5/10 Origin Story and Building the MVP Nathan drills into the specifics of Matt's founding story, interrupting to clarify the exact motivation behind checking employee timesheets and the equity split with his co-founder. Matt explains how an MVP saved him thousands on payroll in his previous franchise business.8:01–10:43 · Nathan as informed peer 5/10 Navigating Startup Struggles and the Payroll Pivot Matt educates Nathan on why basic timers fail at payroll compared to T-Sheets' timestamp logging architecture. Nathan presses for early revenue figures and ARR milestones during their lean early years.10:43–13:08 · Nathan as informed peer 6/10 Scaling Customer Milestones and Series A Financing Matt deflects disclosing precise customer numbers, forcing Nathan to corner him into bracketed estimates for paying companies and seats. Nathan probes Matt's psychology regarding financial security and risk tolerance.13:10–15:38 · Nathan as informed peer 6/10 Nathan Latka Acquisition of The Top Inbox After an ad read for The Top Inbox, Nathan runs napkin math comparing base platform fees to seat fees and questions why T-Sheets bothers charging a small $16 base fee. Matt explains it is legacy pricing they deliberately avoid tinkering with to keep friction low.15:40–17:43 · Nathan as informed peer 6/10 Product Stickiness and Industry-Leading Retention Matt educates Nathan on SMB retention dynamics and explains why time tracking creates stickier engagement across all employees than back-office payroll tools. Nathan asks technical SaaS metrics questions regarding logo churn and net revenue expansion.17:45–20:00 · Nathan as informed peer 6/10 Data-Driven CAC and Channel Acquisition Strategy Nathan tries to extract concrete figures on payback periods and paid acquisition budgets, rejecting Matt's generic Silicon Valley comparisons. Matt explains their iterative data-driven CAC expansion and contraction cycle.20:00–24:04 · Nathan as informed peer 8/10 Evaluating T-Sheets Annual Recurring Revenue Nathan traps Matt with a target $40M ARR figure and lays out a transparent breakdown of his unit math, forcing Matt to concede Nathan's calculations are accurate. Nathan closes out with the Famous Five and presses Matt on potential acquisition interest.1:12–3:52 · Guest teaching 4/10 Marketplace Reviews and Viral Employee Referrals Nathan immediately challenges Matt on his marketing claim of being the top-rated time tracking software on the market, demanding specific proof. Matt substantiates the claim using Intuit app store metrics and virality via departing employees, while Nathan calculates the unit economics using his own business as an example.3:53–8:01 · Guest teaching 3/10 Origin Story and Building the MVP Nathan drills into the specifics of Matt's founding story, interrupting to clarify the exact motivation behind checking employee timesheets and the equity split with his co-founder. Matt explains how an MVP saved him thousands on payroll in his previous franchise business.8:01–10:43 · Guest teaching 6/10 Navigating Startup Struggles and the Payroll Pivot Matt educates Nathan on why basic timers fail at payroll compared to T-Sheets' timestamp logging architecture. Nathan presses for early revenue figures and ARR milestones during their lean early years.10:43–13:08 · Guest teaching 3/10 Scaling Customer Milestones and Series A Financing Matt deflects disclosing precise customer numbers, forcing Nathan to corner him into bracketed estimates for paying companies and seats. Nathan probes Matt's psychology regarding financial security and risk tolerance.13:10–15:38 · Guest teaching 2/10 Nathan Latka Acquisition of The Top Inbox After an ad read for The Top Inbox, Nathan runs napkin math comparing base platform fees to seat fees and questions why T-Sheets bothers charging a small $16 base fee. Matt explains it is legacy pricing they deliberately avoid tinkering with to keep friction low.15:40–17:43 · Guest teaching 6/10 Product Stickiness and Industry-Leading Retention Matt educates Nathan on SMB retention dynamics and explains why time tracking creates stickier engagement across all employees than back-office payroll tools. Nathan asks technical SaaS metrics questions regarding logo churn and net revenue expansion.17:45–20:00 · Guest teaching 4/10 Data-Driven CAC and Channel Acquisition Strategy Nathan tries to extract concrete figures on payback periods and paid acquisition budgets, rejecting Matt's generic Silicon Valley comparisons. Matt explains their iterative data-driven CAC expansion and contraction cycle.20:00–24:04 · Guest teaching 3/10 Evaluating T-Sheets Annual Recurring Revenue Nathan traps Matt with a target $40M ARR figure and lays out a transparent breakdown of his unit math, forcing Matt to concede Nathan's calculations are accurate. Nathan closes out with the Famous Five and presses Matt on potential acquisition interest.1:12–3:52 · Guest disagreement 2/10 Marketplace Reviews and Viral Employee Referrals Nathan immediately challenges Matt on his marketing claim of being the top-rated time tracking software on the market, demanding specific proof. Matt substantiates the claim using Intuit app store metrics and virality via departing employees, while Nathan calculates the unit economics using his own business as an example.3:53–8:01 · Guest disagreement 1/10 Origin Story and Building the MVP Nathan drills into the specifics of Matt's founding story, interrupting to clarify the exact motivation behind checking employee timesheets and the equity split with his co-founder. Matt explains how an MVP saved him thousands on payroll in his previous franchise business.8:01–10:43 · Guest disagreement 1/10 Navigating Startup Struggles and the Payroll Pivot Matt educates Nathan on why basic timers fail at payroll compared to T-Sheets' timestamp logging architecture. Nathan presses for early revenue figures and ARR milestones during their lean early years.10:43–13:08 · Guest disagreement 3/10 Scaling Customer Milestones and Series A Financing Matt deflects disclosing precise customer numbers, forcing Nathan to corner him into bracketed estimates for paying companies and seats. Nathan probes Matt's psychology regarding financial security and risk tolerance.13:10–15:38 · Guest disagreement 2/10 Nathan Latka Acquisition of The Top Inbox After an ad read for The Top Inbox, Nathan runs napkin math comparing base platform fees to seat fees and questions why T-Sheets bothers charging a small $16 base fee. Matt explains it is legacy pricing they deliberately avoid tinkering with to keep friction low.15:40–17:43 · Guest disagreement 2/10 Product Stickiness and Industry-Leading Retention Matt educates Nathan on SMB retention dynamics and explains why time tracking creates stickier engagement across all employees than back-office payroll tools. Nathan asks technical SaaS metrics questions regarding logo churn and net revenue expansion.17:45–20:00 · Guest disagreement 3/10 Data-Driven CAC and Channel Acquisition Strategy Nathan tries to extract concrete figures on payback periods and paid acquisition budgets, rejecting Matt's generic Silicon Valley comparisons. Matt explains their iterative data-driven CAC expansion and contraction cycle.20:00–24:04 · Guest disagreement 3/10 Evaluating T-Sheets Annual Recurring Revenue Nathan traps Matt with a target $40M ARR figure and lays out a transparent breakdown of his unit math, forcing Matt to concede Nathan's calculations are accurate. Nathan closes out with the Famous Five and presses Matt on potential acquisition interest.1:12–3:52 · Nathan pushing back 5/10 Marketplace Reviews and Viral Employee Referrals Nathan immediately challenges Matt on his marketing claim of being the top-rated time tracking software on the market, demanding specific proof. Matt substantiates the claim using Intuit app store metrics and virality via departing employees, while Nathan calculates the unit economics using his own business as an example.3:53–8:01 · Nathan pushing back 4/10 Origin Story and Building the MVP Nathan drills into the specifics of Matt's founding story, interrupting to clarify the exact motivation behind checking employee timesheets and the equity split with his co-founder. Matt explains how an MVP saved him thousands on payroll in his previous franchise business.8:01–10:43 · Nathan pushing back 4/10 Navigating Startup Struggles and the Payroll Pivot Matt educates Nathan on why basic timers fail at payroll compared to T-Sheets' timestamp logging architecture. Nathan presses for early revenue figures and ARR milestones during their lean early years.10:43–13:08 · Nathan pushing back 6/10 Scaling Customer Milestones and Series A Financing Matt deflects disclosing precise customer numbers, forcing Nathan to corner him into bracketed estimates for paying companies and seats. Nathan probes Matt's psychology regarding financial security and risk tolerance.13:10–15:38 · Nathan pushing back 5/10 Nathan Latka Acquisition of The Top Inbox After an ad read for The Top Inbox, Nathan runs napkin math comparing base platform fees to seat fees and questions why T-Sheets bothers charging a small $16 base fee. Matt explains it is legacy pricing they deliberately avoid tinkering with to keep friction low.15:40–17:43 · Nathan pushing back 4/10 Product Stickiness and Industry-Leading Retention Matt educates Nathan on SMB retention dynamics and explains why time tracking creates stickier engagement across all employees than back-office payroll tools. Nathan asks technical SaaS metrics questions regarding logo churn and net revenue expansion.17:45–20:00 · Nathan pushing back 6/10 Data-Driven CAC and Channel Acquisition Strategy Nathan tries to extract concrete figures on payback periods and paid acquisition budgets, rejecting Matt's generic Silicon Valley comparisons. Matt explains their iterative data-driven CAC expansion and contraction cycle.20:00–24:04 · Nathan pushing back 6/10 Evaluating T-Sheets Annual Recurring Revenue Nathan traps Matt with a target $40M ARR figure and lays out a transparent breakdown of his unit math, forcing Matt to concede Nathan's calculations are accurate. Nathan closes out with the Famous Five and presses Matt on potential acquisition interest.

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

0:00 · Nathan 41.9% · guest 58.1%0:00 · Nathan 41.9% · guest 58.1%3:00 · Nathan 21.8% · guest 78.2%3:00 · Nathan 21.8% · guest 78.2%6:00 · Nathan 22.2% · guest 77.8%6:00 · Nathan 22.2% · guest 77.8%9:00 · Nathan 30.3% · guest 69.7%9:00 · Nathan 30.3% · guest 69.7%12:00 · Nathan 71.9% · guest 28.1%12:00 · Nathan 71.9% · guest 28.1%15:00 · Nathan 30% · guest 70%15:00 · Nathan 30% · guest 70%18:00 · Nathan 45.4% · guest 54.6%18:00 · Nathan 45.4% · guest 54.6%21:00 · Nathan 31.6% · guest 68.4%21:00 · Nathan 31.6% · guest 68.4%24:00 · Nathan 91.5% · guest 8.5%24:00 · Nathan 91.5% · guest 8.5%
Sharpest disagreement ▶ 21:40 Balking at buyout hypothetical

Matt pushes back against Nathan's abrupt question asking if he would sell the company for $250M to Intuit's CEO, asking what kind of question that even is.

 Hardest push from Nathan ▶ 1:14 Interrogating top-rated claim

Nathan refuses to let Matt glide past his promotional tagline, cutting in immediately to demand hard evidence for how he knows T-Sheets is the top-requested software.

 Biggest teaching moment ▶ 9:43 Payroll timestamping vs basic timers

Matt clearly educates Nathan on why conventional elapsed-time trackers fail to serve payroll requirements due to lack of verified audit logs and database timestamps.

 Nathan holds their own ▶ 20:15 Nathan details ARR mathematical model

When Matt questions where the $40M ARR figure came from, Nathan walks through seat count, monthly price per seat, and base fee multipliers to estimate ~$36M ARR on the spot.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Marketplace Reviews and Viral Employee Referrals 6425 Nathan immediately challenges Matt on his marketing claim of being the top-rated time tracking software on the market, demanding specific proof. Matt substantiates the claim using Intuit app store metrics and virality via departing employees, while Nathan calculates the unit economics using his own business as an example.
Origin Story and Building the MVP 5314 Nathan drills into the specifics of Matt's founding story, interrupting to clarify the exact motivation behind checking employee timesheets and the equity split with his co-founder. Matt explains how an MVP saved him thousands on payroll in his previous franchise business.
Navigating Startup Struggles and the Payroll Pivot 5614 Matt educates Nathan on why basic timers fail at payroll compared to T-Sheets' timestamp logging architecture. Nathan presses for early revenue figures and ARR milestones during their lean early years.
Scaling Customer Milestones and Series A Financing 6336 Matt deflects disclosing precise customer numbers, forcing Nathan to corner him into bracketed estimates for paying companies and seats. Nathan probes Matt's psychology regarding financial security and risk tolerance.
Nathan Latka Acquisition of The Top Inbox 6225 After an ad read for The Top Inbox, Nathan runs napkin math comparing base platform fees to seat fees and questions why T-Sheets bothers charging a small $16 base fee. Matt explains it is legacy pricing they deliberately avoid tinkering with to keep friction low.
Product Stickiness and Industry-Leading Retention 6624 Matt educates Nathan on SMB retention dynamics and explains why time tracking creates stickier engagement across all employees than back-office payroll tools. Nathan asks technical SaaS metrics questions regarding logo churn and net revenue expansion.
Data-Driven CAC and Channel Acquisition Strategy 6436 Nathan tries to extract concrete figures on payback periods and paid acquisition budgets, rejecting Matt's generic Silicon Valley comparisons. Matt explains their iterative data-driven CAC expansion and contraction cycle.
Evaluating T-Sheets Annual Recurring Revenue 8336 Nathan traps Matt with a target $40M ARR figure and lays out a transparent breakdown of his unit math, forcing Matt to concede Nathan's calculations are accurate. Nathan closes out with the Famous Five and presses Matt on potential acquisition interest.

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