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May 6, 2018 · 18m · top-founders

1016 How He Managed Launching 2 $100m+ Companies At Once

Vijay Bassani · 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 episode of The Top Entrepreneurs Podcast, host Nathan Latka interviews serial founder Vijay Bassani to analyze his dual-founding journey, past $280M exit to HP, and the SaaS unit economics scaling mid-market cybersecurity firm Sigilent past $8 million in ARR.

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 47.5% of the talking time here. How this is scored →

Nathan as informed peer 5.3 Guest teaching 3.0 Guest disagreement 1.3 Nathan pushing back 3.3
05100:0010:000:49–7:22 · Nathan as informed peer 5/10 Introducing Vijay Bassani and Sigilent Overview Nathan probes Vijay on the timeline of building two venture-backed companies concurrently and AppIQ's acquisition. He politely interrupts Vijay's lengthy overview of the cybersecurity sector to keep the conversation focused on founder history and metrics.7:22–11:36 · Nathan as informed peer 6/10 Customer Acquisition Strategy and Channel Partners Nathan evaluates Sigilent's go-to-market model, joking about their generous channel partner cuts and scrutinizing their 20-month CAC payback period against their negative net revenue churn metrics.11:38–15:33 · Nathan as informed peer 7/10 Host Announcement: Acquisition of The Top Inbox After an ad announcement, Nathan computes Sigilent's LTV, fully weighted CAC, and ARR run-rate on the fly. Vijay corrects Nathan's assumption of pure-SaaS 85%+ gross margins by explaining the cost of human service delivery.15:35–17:45 · Nathan as informed peer 3/10 The Famous Five Rapid-Fire Questions During the Famous Five rapid fire, Vijay resists the premise of wishing he did anything differently, prompting Nathan to reframe the prompt from regret to knowledge acquisition.0:49–7:22 · Guest teaching 4/10 Introducing Vijay Bassani and Sigilent Overview Nathan probes Vijay on the timeline of building two venture-backed companies concurrently and AppIQ's acquisition. He politely interrupts Vijay's lengthy overview of the cybersecurity sector to keep the conversation focused on founder history and metrics.7:22–11:36 · Guest teaching 3/10 Customer Acquisition Strategy and Channel Partners Nathan evaluates Sigilent's go-to-market model, joking about their generous channel partner cuts and scrutinizing their 20-month CAC payback period against their negative net revenue churn metrics.11:38–15:33 · Guest teaching 4/10 Host Announcement: Acquisition of The Top Inbox After an ad announcement, Nathan computes Sigilent's LTV, fully weighted CAC, and ARR run-rate on the fly. Vijay corrects Nathan's assumption of pure-SaaS 85%+ gross margins by explaining the cost of human service delivery.15:35–17:45 · Guest teaching 1/10 The Famous Five Rapid-Fire Questions During the Famous Five rapid fire, Vijay resists the premise of wishing he did anything differently, prompting Nathan to reframe the prompt from regret to knowledge acquisition.0:49–7:22 · Guest disagreement 1/10 Introducing Vijay Bassani and Sigilent Overview Nathan probes Vijay on the timeline of building two venture-backed companies concurrently and AppIQ's acquisition. He politely interrupts Vijay's lengthy overview of the cybersecurity sector to keep the conversation focused on founder history and metrics.7:22–11:36 · Guest disagreement 1/10 Customer Acquisition Strategy and Channel Partners Nathan evaluates Sigilent's go-to-market model, joking about their generous channel partner cuts and scrutinizing their 20-month CAC payback period against their negative net revenue churn metrics.11:38–15:33 · Guest disagreement 1/10 Host Announcement: Acquisition of The Top Inbox After an ad announcement, Nathan computes Sigilent's LTV, fully weighted CAC, and ARR run-rate on the fly. Vijay corrects Nathan's assumption of pure-SaaS 85%+ gross margins by explaining the cost of human service delivery.15:35–17:45 · Guest disagreement 2/10 The Famous Five Rapid-Fire Questions During the Famous Five rapid fire, Vijay resists the premise of wishing he did anything differently, prompting Nathan to reframe the prompt from regret to knowledge acquisition.0:49–7:22 · Nathan pushing back 4/10 Introducing Vijay Bassani and Sigilent Overview Nathan probes Vijay on the timeline of building two venture-backed companies concurrently and AppIQ's acquisition. He politely interrupts Vijay's lengthy overview of the cybersecurity sector to keep the conversation focused on founder history and metrics.7:22–11:36 · Nathan pushing back 3/10 Customer Acquisition Strategy and Channel Partners Nathan evaluates Sigilent's go-to-market model, joking about their generous channel partner cuts and scrutinizing their 20-month CAC payback period against their negative net revenue churn metrics.11:38–15:33 · Nathan pushing back 3/10 Host Announcement: Acquisition of The Top Inbox After an ad announcement, Nathan computes Sigilent's LTV, fully weighted CAC, and ARR run-rate on the fly. Vijay corrects Nathan's assumption of pure-SaaS 85%+ gross margins by explaining the cost of human service delivery.15:35–17:45 · Nathan pushing back 3/10 The Famous Five Rapid-Fire Questions During the Famous Five rapid fire, Vijay resists the premise of wishing he did anything differently, prompting Nathan to reframe the prompt from regret to knowledge acquisition.

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

0:00 · Nathan 55.1% · guest 44.9%0:00 · Nathan 55.1% · guest 44.9%3:00 · Nathan 18.2% · guest 81.8%3:00 · Nathan 18.2% · guest 81.8%6:00 · Nathan 52% · guest 48%6:00 · Nathan 52% · guest 48%9:00 · Nathan 43% · guest 57%9:00 · Nathan 43% · guest 57%12:00 · Nathan 69.6% · guest 30.4%12:00 · Nathan 69.6% · guest 30.4%15:00 · Nathan 38.3% · guest 61.7%15:00 · Nathan 38.3% · guest 61.7%18:00 · Nathan 97% · guest 3%18:00 · Nathan 97% · guest 3%
Sharpest disagreement ▶ 17:02 Vijay rejects reflection prompt

Vijay resists Nathan's question about what he wishes he knew at 20 by stating he wouldn't do anything differently.

 Hardest push from Nathan ▶ 5:37 Host cuts off industry macro explanation

Nathan cuts Vijay off mid-explanation of mid-market security challenges to refocus the episode on Vijay's specific decisions and company launch timeline.

 Biggest teaching moment ▶ 15:00 Correction on SaaS gross margins

Vijay corrects Nathan's assumption that the business achieves typical 85%+ software margins, explaining that their human security monitoring layer caps margins at around 70%.

 Nathan holds their own ▶ 13:03 Host calculates LTV and blended CAC

Nathan quickly translates customer contract values, churn rates, and payback periods into exact lifetime values and fully weighted acquisition costs.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Introducing Vijay Bassani and Sigilent Overview 5414 Nathan probes Vijay on the timeline of building two venture-backed companies concurrently and AppIQ's acquisition. He politely interrupts Vijay's lengthy overview of the cybersecurity sector to keep the conversation focused on founder history and metrics.
Customer Acquisition Strategy and Channel Partners 6313 Nathan evaluates Sigilent's go-to-market model, joking about their generous channel partner cuts and scrutinizing their 20-month CAC payback period against their negative net revenue churn metrics.
Host Announcement: Acquisition of The Top Inbox 7413 After an ad announcement, Nathan computes Sigilent's LTV, fully weighted CAC, and ARR run-rate on the fly. Vijay corrects Nathan's assumption of pure-SaaS 85%+ gross margins by explaining the cost of human service delivery.
The Famous Five Rapid-Fire Questions 3123 During the Famous Five rapid fire, Vijay resists the premise of wishing he did anything differently, prompting Nathan to reframe the prompt from regret to knowledge acquisition.

Statements from this episode (13)

Assertion Not checkable as stated
Bassani: Cygilant's average customer pays $25k to $50k annually
“We tend to focus on sub five percent employee company segment. And the average payment is anywhere from, you know, 25,000 dollars to 50,000 dollars per year.”
Vijay Bassani May 6, 2018 ▶ 1:56
Assertion Not checkable as stated
Bassani: 75% of mid-market companies have two or fewer security staff
“In our survey, we found out that 75% of these market segment customers tend to have two or less security professionals on their team.”
Vijay Bassani May 6, 2018 ▶ 5:12
Assertion Supported
Bassani: AppIQ was acquired by Hewlett-Packard for $280M
“It was sold for about two hundred eighty million dollars.”
Vijay Bassani May 6, 2018 ▶ 6:45
Disclosure
Bassani: Cygilant has raised a total of $38M to date
“Initially, we bootstrapped, and then we raised our money. To date, we have raised a total of thirty-eight million dollars.”
Vijay Bassani May 6, 2018 ▶ 7:12
Disclosure
Bassani: Cygilant reaches total headcount of 170 employees
“In total, we have 170 people in the company.”
Vijay Bassani May 6, 2018 ▶ 8:06
Disclosure
Bassani: Cygilant pays channel partners 10% to 30% of ACV
“We tend to give anywhere from 10 to 30% of the ACV.”
Vijay Bassani May 6, 2018 ▶ 8:41
Assertion Not checkable as stated
Bassani: Cygilant's customer payback period is over 20 months
“We are close at about 20 plus.”
Vijay Bassani May 6, 2018 ▶ 9:11
Assertion Not checkable as stated
Bassani: Cygilant has an annual logo churn of 2% to 5%
“On a dollar basis, on a logo basis, we probably have, you know, anywhere from two to five percent churn rate.”
Vijay Bassani May 6, 2018 ▶ 9:57
Assertion Not checkable as stated
Bassani: Cygilant operates at net negative revenue churn
“Yes, and the dollar churn rate, including the expansion and cross-sell, it's, we have negative churn rate.”
Vijay Bassani May 6, 2018 ▶ 10:08
Assertion Not checkable as stated
Bassani: Cygilant's fully weighted CAC is $40,000 to $50,000
“Something around, around that 40 to 50 grand is gonna be our, you know, tack.”
Vijay Bassani May 6, 2018 ▶ 13:30
Prediction Not checkable as stated
Bassani: Cygilant expects to become cashflow positive in 2019
“We expect to be cashflow positive sometime next year.”
Vijay Bassani May 6, 2018 ▶ 14:38
Disclosure
Bassani: Cygilant targets 70%+ gross margin despite service component
“We also have actually service component attached to it. We are driving towards a 70 plus percent gross margin.”
Vijay Bassani May 6, 2018 ▶ 15:12
Assertion Not checkable as stated
Cygilant exceeds $8M ARR across 300+ customers, doubling YoY
“He has over 300 customers doing over eight million dollars a year in revenue, almost doubling year over year for the past three years on track to continue doing that.”
Nathan Latka May 6, 2018 ▶ 18:06
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