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Nov 1, 2020 · 25m · top-founders

Cylynt Security SaaS To Break $10m Up From $6m Last Year, Bootstrapped

Ted Miracco · 15m 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 with Nathan Latka, Cylynt co-founder and CEO Ted Miracco explains how his enterprise telemetry and anti-piracy SaaS company bootstrapped to profitability and scaled toward $10 million in ARR. Miracco breaks down Cylynt's compliance monetization model, capital-efficient sales metrics, and strategic Dublin-based engineering workforce.

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 33.6% of the talking time here. How this is scored →

Nathan as informed peer 5.8 Guest teaching 2.8 Guest disagreement 1.4 Nathan pushing back 3.8
05100:0010:0020:000:19–3:57 · Nathan as informed peer 3/10 Podcast Subscription Announcement and Member Benefits The segment begins with a promotional message and introductory housekeeping before Nathan introduces Ted, who outlines Cylynt's origin and focus on on-premise software anti-piracy telemetry.3:58–6:37 · Nathan as informed peer 5/10 Origin Story, AWR Exit, and Bootstrapping Cylynt Nathan probes into the financial details of Ted's previous exit with AWR and the personal capital required to bootstrap Cylynt to profitability.6:37–12:32 · Nathan as informed peer 6/10 Pricing Strategy, Customer Base, and Anti-Piracy Use Cases Ted explains how litigation credibility helped land initial enterprise clients, and Nathan synthesizes the exact customer use case to ensure clarity for his audience.12:34–18:21 · Nathan as informed peer 7/10 Mid-Roll Sponsorship: Flippa Valuation Tool Nathan breaks down unit economics including CAC, gross churn, and mathematically verifies Ted's net revenue retention at 125 percent.18:21–23:26 · Nathan as informed peer 8/10 Sales Quota Models, Expansion Strategy, and Revenue Growth Nathan pushes on Ted's sales quota model, noting that a 3x quota-to-OTE ratio is below SaaS standards, and verifies Cylynt's historical revenue timeline toward $10M ARR.0:19–3:57 · Guest teaching 2/10 Podcast Subscription Announcement and Member Benefits The segment begins with a promotional message and introductory housekeeping before Nathan introduces Ted, who outlines Cylynt's origin and focus on on-premise software anti-piracy telemetry.3:58–6:37 · Guest teaching 2/10 Origin Story, AWR Exit, and Bootstrapping Cylynt Nathan probes into the financial details of Ted's previous exit with AWR and the personal capital required to bootstrap Cylynt to profitability.6:37–12:32 · Guest teaching 3/10 Pricing Strategy, Customer Base, and Anti-Piracy Use Cases Ted explains how litigation credibility helped land initial enterprise clients, and Nathan synthesizes the exact customer use case to ensure clarity for his audience.12:34–18:21 · Guest teaching 3/10 Mid-Roll Sponsorship: Flippa Valuation Tool Nathan breaks down unit economics including CAC, gross churn, and mathematically verifies Ted's net revenue retention at 125 percent.18:21–23:26 · Guest teaching 4/10 Sales Quota Models, Expansion Strategy, and Revenue Growth Nathan pushes on Ted's sales quota model, noting that a 3x quota-to-OTE ratio is below SaaS standards, and verifies Cylynt's historical revenue timeline toward $10M ARR.0:19–3:57 · Guest disagreement 1/10 Podcast Subscription Announcement and Member Benefits The segment begins with a promotional message and introductory housekeeping before Nathan introduces Ted, who outlines Cylynt's origin and focus on on-premise software anti-piracy telemetry.3:58–6:37 · Guest disagreement 1/10 Origin Story, AWR Exit, and Bootstrapping Cylynt Nathan probes into the financial details of Ted's previous exit with AWR and the personal capital required to bootstrap Cylynt to profitability.6:37–12:32 · Guest disagreement 1/10 Pricing Strategy, Customer Base, and Anti-Piracy Use Cases Ted explains how litigation credibility helped land initial enterprise clients, and Nathan synthesizes the exact customer use case to ensure clarity for his audience.12:34–18:21 · Guest disagreement 2/10 Mid-Roll Sponsorship: Flippa Valuation Tool Nathan breaks down unit economics including CAC, gross churn, and mathematically verifies Ted's net revenue retention at 125 percent.18:21–23:26 · Guest disagreement 2/10 Sales Quota Models, Expansion Strategy, and Revenue Growth Nathan pushes on Ted's sales quota model, noting that a 3x quota-to-OTE ratio is below SaaS standards, and verifies Cylynt's historical revenue timeline toward $10M ARR.0:19–3:57 · Nathan pushing back 1/10 Podcast Subscription Announcement and Member Benefits The segment begins with a promotional message and introductory housekeeping before Nathan introduces Ted, who outlines Cylynt's origin and focus on on-premise software anti-piracy telemetry.3:58–6:37 · Nathan pushing back 4/10 Origin Story, AWR Exit, and Bootstrapping Cylynt Nathan probes into the financial details of Ted's previous exit with AWR and the personal capital required to bootstrap Cylynt to profitability.6:37–12:32 · Nathan pushing back 3/10 Pricing Strategy, Customer Base, and Anti-Piracy Use Cases Ted explains how litigation credibility helped land initial enterprise clients, and Nathan synthesizes the exact customer use case to ensure clarity for his audience.12:34–18:21 · Nathan pushing back 5/10 Mid-Roll Sponsorship: Flippa Valuation Tool Nathan breaks down unit economics including CAC, gross churn, and mathematically verifies Ted's net revenue retention at 125 percent.18:21–23:26 · Nathan pushing back 6/10 Sales Quota Models, Expansion Strategy, and Revenue Growth Nathan pushes on Ted's sales quota model, noting that a 3x quota-to-OTE ratio is below SaaS standards, and verifies Cylynt's historical revenue timeline toward $10M ARR.

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

0:00 · Nathan 60.3% · guest 39.7%0:00 · Nathan 60.3% · guest 39.7%3:00 · Nathan 17.1% · guest 82.9%3:00 · Nathan 17.1% · guest 82.9%6:00 · Nathan 15.1% · guest 84.9%6:00 · Nathan 15.1% · guest 84.9%9:00 · Nathan 23.3% · guest 76.7%9:00 · Nathan 23.3% · guest 76.7%12:00 · Nathan 55.9% · guest 44.1%12:00 · Nathan 55.9% · guest 44.1%15:00 · Nathan 30.5% · guest 69.5%15:00 · Nathan 30.5% · guest 69.5%18:00 · Nathan 31.4% · guest 68.6%18:00 · Nathan 31.4% · guest 68.6%21:00 · Nathan 34.7% · guest 65.3%21:00 · Nathan 34.7% · guest 65.3%24:00 · Nathan 33.4% · guest 66.6%24:00 · Nathan 33.4% · guest 66.6%
Sharpest disagreement ▶ 22:07 Ted clarifies the first year revenue timeline

Ted firmly corrects Nathan's timeline interpretation, clarifying that late 2014 was a mid-year start and 2015 was their actual first full year of revenue.

 Hardest push from Nathan ▶ 19:39 Nathan challenges the quota multiple

Nathan refuses to let a 3x quota-to-OTE ratio pass without scrutiny, pressing Ted on why it is lower than the typical 5x-6x SaaS benchmark.

 Biggest teaching moment ▶ 8:48 Ted explains the monetization gray area

Ted educates Nathan on software licensing dynamics, explaining that telemetry helps monetize the gray area of inadvertent overuse rather than fueling hostile litigation.

 Nathan holds their own ▶ 16:00 Nathan calculates net revenue retention formula

Nathan immediately catches the nuance between gross churn and expansion to calculate a clean 125 percent net revenue retention figure.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Podcast Subscription Announcement and Member Benefits 3211 The segment begins with a promotional message and introductory housekeeping before Nathan introduces Ted, who outlines Cylynt's origin and focus on on-premise software anti-piracy telemetry.
Origin Story, AWR Exit, and Bootstrapping Cylynt 5214 Nathan probes into the financial details of Ted's previous exit with AWR and the personal capital required to bootstrap Cylynt to profitability.
Pricing Strategy, Customer Base, and Anti-Piracy Use Cases 6313 Ted explains how litigation credibility helped land initial enterprise clients, and Nathan synthesizes the exact customer use case to ensure clarity for his audience.
Mid-Roll Sponsorship: Flippa Valuation Tool 7325 Nathan breaks down unit economics including CAC, gross churn, and mathematically verifies Ted's net revenue retention at 125 percent.
Sales Quota Models, Expansion Strategy, and Revenue Growth 8426 Nathan pushes on Ted's sales quota model, noting that a 3x quota-to-OTE ratio is below SaaS standards, and verifies Cylynt's historical revenue timeline toward $10M ARR.

Statements from this episode (17)

Disclosure
Cylynt expands beyond anti-piracy to on-premise software usage analytics.
“We're now working on usage analytics and we're, we've expanded our perspective and we've rebranded as silent, you know, today. As part of a broader vision to give on-premise companies, on-premise software vendors, the same kind of visibility that SaaS companie…”
Ted Miracco Nov 1, 2020 ▶ 3:27
Assertion Supported
Cadence bought AWR Corporation from National Instruments for $160 million.
“So Cadence Design Systems bought it from National Instruments, yeah, for around a 160. Correct.”
Ted Miracco Nov 1, 2020 ▶ 5:03
Assertion Not checkable as stated
Cylynt achieved profitability in 2018 without raising outside venture funding.
“We became profitable around 20 18. And you know, the company's has no funding, you know, we're self self-financed and we're profitable.”
Ted Miracco Nov 1, 2020 ▶ 5:32
Disclosure
Cylynt founders personally invested $2M to $3M before reaching profitability.
“We put a bet probably in the two to three million dollars into the company over, over that period of time.”
Ted Miracco Nov 1, 2020 ▶ 5:54
Insight
Miracco advises founders with capital to avoid early VC funding dilution.
“The dilution and the strings that can come with the early funding, It can be very dilutive to founders, so I would advise against that if you have the financial wherewithal to not have to do that.”
Ted Miracco Nov 1, 2020 ▶ 6:22
Disclosure
Cylynt charges roughly $1,000 per user per month for telemetry software.
“Around, around a thousand dollars per user per month.”
Ted Miracco Nov 1, 2020 ▶ 6:44
Disclosure
Cylynt serves approximately 1,500 total users averaging 10 seats per customer.
“Probably around 10, I would say on average, and we have about, you know, we have a couple with close to a hundred users, so they kind of tip the scales a little bit, but I would say we have about 1500 users.”
Ted Miracco Nov 1, 2020 ▶ 6:56
Insight
Miracco says resolving software license overuse rarely leads to hostile litigation.
“A lot of clients kind of think that this is a hostile discussion or leads to litigation. And that's the exception. That's not the rule. In most cases, you know, software companies want to use, they want to pay for the intellectual property that's running their…”
Ted Miracco Nov 1, 2020 ▶ 9:51
Assertion Not checkable as stated
Cylynt generated about $1M in revenue during its first full year.
“Yeah, it was about a million dollars.”
Ted Miracco Nov 1, 2020 ▶ 14:14
Assertion Not checkable as stated
Cylynt spends $100K in CAC to land a $120K ACV account.
“We spend probably about a 100,000 dollars to get into that account.”
Ted Miracco Nov 1, 2020 ▶ 15:21
Assertion Not checkable as stated
Cylynt experiences an annual customer churn rate of about 2.5 percent.
“Our churn is about two and a half percent.”
Ted Miracco Nov 1, 2020 ▶ 15:36
Assertion Not checkable as stated
Cylynt maintains a net revenue retention rate of approximately 125 percent.
“No, our gross retention is, is close to a hundred percent. Our increase, our net is more like a 125%.”
Ted Miracco Nov 1, 2020 ▶ 16:05
Disclosure
Cylynt assigns enterprise sales reps an annual quota of $1 million.
“Generally what we're looking at is about a million dollars a year.”
Ted Miracco Nov 1, 2020 ▶ 18:35
Prediction Not checkable as stated
Cylynt is on track to hit a $10M revenue run rate.
“This year target is around 10.”
Ted Miracco Nov 1, 2020 ▶ 21:04
Assertion Not checkable as stated
Cylynt finished fiscal year 2019 with around $6M in revenue.
“Around six.”
Ted Miracco Nov 1, 2020 ▶ 21:13
Assertion Not checkable as stated
Cylynt consistently maintains 50% to 70% year-over-year revenue growth.
“Yeah, you know, we, we've had about, we, we've been pretty consistent in having about a 50 to 70% year-over-year growth, so it's, it doesn't vary that much from year to year.”
Ted Miracco Nov 1, 2020 ▶ 21:31
Insight
Ramping new telemetry enterprise accounts to full success takes three years.
“But you know, with new logos, it usually takes about three years to take the company from an initial deployment to being very successful. It's a, that's a long, you know, cause you have to start gathering data. There's the telemetry data that comes in and it j…”
Ted Miracco Nov 1, 2020 ▶ 23:05
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