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Sep 10, 2018 · 19m · top-founders

1143 Eloqua Founders Launch New Relationship Tool, $600k ARR first 5 Months, $7m Raised

Nathan Latka · 9m spoken Paul Teshima · 8m 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, Nathan Latka interviews Nudge.ai CEO and former Eloqua executive Paul Teshima about building a metadata-driven relationship intelligence platform, securing $7 million in venture funding, and scaling the startup to $60,000 in monthly recurring revenue across 30 enterprise clients.

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 52.7% of the talking time here. How this is scored →

Nathan as informed peer 5.8 Guest teaching 4.0 Guest disagreement 1.6 Nathan pushing back 3.8
05100:0010:002:14–6:44 · Nathan as informed peer 6/10 Understanding Relationship Intelligence and Market Differentiation Nathan probes into Nudge's differentiation and privacy safeguards, citing market competitors like Conspire. Paul articulates how communication metadata and frequency signals establish relationship strength without accessing email content.6:48–11:18 · Nathan as informed peer 6/10 Sponsor Message: Emma Email Marketing Nathan challenges Paul regarding his post-acquisition tenure at Oracle, jokingly insisting it had to be an earn-out retention deal. Paul clarifies that there was no revesting and explains why investors actively pursue experienced second-time founders.11:19–14:11 · Nathan as informed peer 7/10 User Distribution, Enterprise Traction, and Monthly Revenue Nathan calculates revenue by multiplying total seats by the list price, leading Paul to correct him on the freemium versus paid user split. Nathan quickly recalibrates his estimates to align with Paul's actual paying customer numbers.14:11–17:44 · Nathan as informed peer 7/10 Enterprise Onboarding, Retention Metrics, and Churn Benchmarks Nathan explores onboarding retention and benchmark churn rates, expressing initial surprise at a 35 percent retention rate until Paul clarifies it includes free users. Paul explains why gross MRR churn offers a cleaner operational signal than net revenue retention.17:45–18:47 · Nathan as informed peer 3/10 The Famous Five Rapid-Fire Questions The interview wraps up smoothly with the standard rapid-fire questions covering Paul's book choices, tool preferences, and founder advice.2:14–6:44 · Guest teaching 5/10 Understanding Relationship Intelligence and Market Differentiation Nathan probes into Nudge's differentiation and privacy safeguards, citing market competitors like Conspire. Paul articulates how communication metadata and frequency signals establish relationship strength without accessing email content.6:48–11:18 · Guest teaching 4/10 Sponsor Message: Emma Email Marketing Nathan challenges Paul regarding his post-acquisition tenure at Oracle, jokingly insisting it had to be an earn-out retention deal. Paul clarifies that there was no revesting and explains why investors actively pursue experienced second-time founders.11:19–14:11 · Guest teaching 5/10 User Distribution, Enterprise Traction, and Monthly Revenue Nathan calculates revenue by multiplying total seats by the list price, leading Paul to correct him on the freemium versus paid user split. Nathan quickly recalibrates his estimates to align with Paul's actual paying customer numbers.14:11–17:44 · Guest teaching 6/10 Enterprise Onboarding, Retention Metrics, and Churn Benchmarks Nathan explores onboarding retention and benchmark churn rates, expressing initial surprise at a 35 percent retention rate until Paul clarifies it includes free users. Paul explains why gross MRR churn offers a cleaner operational signal than net revenue retention.17:45–18:47 · Guest teaching 0/10 The Famous Five Rapid-Fire Questions The interview wraps up smoothly with the standard rapid-fire questions covering Paul's book choices, tool preferences, and founder advice.2:14–6:44 · Guest disagreement 2/10 Understanding Relationship Intelligence and Market Differentiation Nathan probes into Nudge's differentiation and privacy safeguards, citing market competitors like Conspire. Paul articulates how communication metadata and frequency signals establish relationship strength without accessing email content.6:48–11:18 · Guest disagreement 3/10 Sponsor Message: Emma Email Marketing Nathan challenges Paul regarding his post-acquisition tenure at Oracle, jokingly insisting it had to be an earn-out retention deal. Paul clarifies that there was no revesting and explains why investors actively pursue experienced second-time founders.11:19–14:11 · Guest disagreement 2/10 User Distribution, Enterprise Traction, and Monthly Revenue Nathan calculates revenue by multiplying total seats by the list price, leading Paul to correct him on the freemium versus paid user split. Nathan quickly recalibrates his estimates to align with Paul's actual paying customer numbers.14:11–17:44 · Guest disagreement 1/10 Enterprise Onboarding, Retention Metrics, and Churn Benchmarks Nathan explores onboarding retention and benchmark churn rates, expressing initial surprise at a 35 percent retention rate until Paul clarifies it includes free users. Paul explains why gross MRR churn offers a cleaner operational signal than net revenue retention.17:45–18:47 · Guest disagreement 0/10 The Famous Five Rapid-Fire Questions The interview wraps up smoothly with the standard rapid-fire questions covering Paul's book choices, tool preferences, and founder advice.2:14–6:44 · Nathan pushing back 4/10 Understanding Relationship Intelligence and Market Differentiation Nathan probes into Nudge's differentiation and privacy safeguards, citing market competitors like Conspire. Paul articulates how communication metadata and frequency signals establish relationship strength without accessing email content.6:48–11:18 · Nathan pushing back 5/10 Sponsor Message: Emma Email Marketing Nathan challenges Paul regarding his post-acquisition tenure at Oracle, jokingly insisting it had to be an earn-out retention deal. Paul clarifies that there was no revesting and explains why investors actively pursue experienced second-time founders.11:19–14:11 · Nathan pushing back 5/10 User Distribution, Enterprise Traction, and Monthly Revenue Nathan calculates revenue by multiplying total seats by the list price, leading Paul to correct him on the freemium versus paid user split. Nathan quickly recalibrates his estimates to align with Paul's actual paying customer numbers.14:11–17:44 · Nathan pushing back 4/10 Enterprise Onboarding, Retention Metrics, and Churn Benchmarks Nathan explores onboarding retention and benchmark churn rates, expressing initial surprise at a 35 percent retention rate until Paul clarifies it includes free users. Paul explains why gross MRR churn offers a cleaner operational signal than net revenue retention.17:45–18:47 · Nathan pushing back 1/10 The Famous Five Rapid-Fire Questions The interview wraps up smoothly with the standard rapid-fire questions covering Paul's book choices, tool preferences, and founder advice.

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

0:00 · Nathan 83.1% · guest 16.9%0:00 · Nathan 83.1% · guest 16.9%3:00 · Nathan 40.4% · guest 59.6%3:00 · Nathan 40.4% · guest 59.6%6:00 · Nathan 60.5% · guest 39.5%6:00 · Nathan 60.5% · guest 39.5%9:00 · Nathan 38.8% · guest 61.2%9:00 · Nathan 38.8% · guest 61.2%12:00 · Nathan 41.3% · guest 58.7%12:00 · Nathan 41.3% · guest 58.7%15:00 · Nathan 38.8% · guest 61.2%15:00 · Nathan 38.8% · guest 61.2%18:00 · Nathan 76.9% · guest 23.1%18:00 · Nathan 76.9% · guest 23.1%
Sharpest disagreement ▶ 9:03 Paul denies earn-out and revesting claims

Paul directly pushes back against Nathan's accusation that his post-acquisition stay at Oracle was mandated by an earn-out clause, explaining his shares were fully vested.

 Hardest push from Nathan ▶ 9:04 Nathan refuses to believe lack of retention incentives

Nathan explicitly challenges Paul's statement about leaving without an earnout, stating 'I don't believe you' and demanding to know if retention packages existed.

 Biggest teaching moment ▶ 16:52 Gross MRR churn vs net retention breakdown

Paul explains how net retention can hide severe underlying customer churn behind a few expanding large accounts, making gross MRR churn the more critical health metric.

 Nathan holds their own ▶ 3:08 Nathan details Conspire and FullContact history

Nathan showcases strong domain knowledge by bringing up Brad Feld, Conspire's acquisition by FullContact, and its subsequent shutdown to pressure Paul on product differentiation.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Understanding Relationship Intelligence and Market Differentiation 6524 Nathan probes into Nudge's differentiation and privacy safeguards, citing market competitors like Conspire. Paul articulates how communication metadata and frequency signals establish relationship strength without accessing email content.
Sponsor Message: Emma Email Marketing 6435 Nathan challenges Paul regarding his post-acquisition tenure at Oracle, jokingly insisting it had to be an earn-out retention deal. Paul clarifies that there was no revesting and explains why investors actively pursue experienced second-time founders.
User Distribution, Enterprise Traction, and Monthly Revenue 7525 Nathan calculates revenue by multiplying total seats by the list price, leading Paul to correct him on the freemium versus paid user split. Nathan quickly recalibrates his estimates to align with Paul's actual paying customer numbers.
Enterprise Onboarding, Retention Metrics, and Churn Benchmarks 7614 Nathan explores onboarding retention and benchmark churn rates, expressing initial surprise at a 35 percent retention rate until Paul clarifies it includes free users. Paul explains why gross MRR churn offers a cleaner operational signal than net revenue retention.
The Famous Five Rapid-Fire Questions 3001 The interview wraps up smoothly with the standard rapid-fire questions covering Paul's book choices, tool preferences, and founder advice.

Statements from this episode (12)

Assertion Not checkable as stated
Teshima: Nudge.ai has around 20,000 users
“We have about 20,000 users on it today.”
Paul Teshima Sep 10, 2018 ▶ 3:34
Assertion Not checkable as stated
Teshima: Nudge.ai never inspects email or calendar contents
“Well, first thing we never look at the contents of anything that is sent. The contents or the of the calendar or the email. So we're only going to know names and we're going to know the back and forth time and date.”
Paul Teshima Sep 10, 2018 ▶ 5:08
Assertion Not checkable as stated
Teshima: Nudge.ai tracks about 50 million business relationships
“And we, today we track about fifty million business relationships on the platform.”
Paul Teshima Sep 10, 2018 ▶ 6:09
Opinion
Teshima: LinkedIn lacks data on connection strength
“And LinkedIn's great. Don't get me wrong. It's a fantastic business network. It just doesn't have the strength of connection.”
Paul Teshima Sep 10, 2018 ▶ 6:36
Assertion Not publicly verifiable
Teshima: Nudge.ai charges $30 per user per month
“Our stress are straight down the middle product is 30 dollars per user per month. US.”
Paul Teshima Sep 10, 2018 ▶ 8:32
Disclosure
Teshima: Eloqua acquisition by Oracle had no share revesting or earn-out
“There was no revesting. We owned all our shares. We could have walked away on, you know, day one after the acquisition was confirmed.”
Paul Teshima Sep 10, 2018 ▶ 9:11
Assertion Supported
Teshima: Nudge.ai has raised over $7 million USD
“So today we've raised just a little over seven million us.”
Paul Teshima Sep 10, 2018 ▶ 9:40
Insight
Teshima: VCs seek repeat founders to de-risk investments
“I don't think they ever come with that objection. They actually want to be part of the second one. So they're actually looking as an opportunity to de-risk another investment with entrepreneurs who've done it before.”
Paul Teshima Sep 10, 2018 ▶ 10:12
Assertion Not checkable as stated
Teshima: Nudge.ai has over 30 customers with largest at 1,000 seats
“And so we now have over 30 customers. Our largest is a thousand sales seats.”
Paul Teshima Sep 10, 2018 ▶ 11:31
Assertion Not checkable as stated
Teshima: Nudge.ai blended 90-day retention exceeds 35%
“It's north of 35%.”
Paul Teshima Sep 10, 2018 ▶ 15:50
Insight
Teshima: Scaling SaaS businesses must keep monthly gross MRR churn under 1.5%
“Oh, I mean, I always think you got to be under 1.5% of total MRR churn per month as you start to scale. That's the benchmark we use at Eloqua that held us true. And then you always look at a net retention on top of that.”
Paul Teshima Sep 10, 2018 ▶ 16:41
Insight
Teshima: Net retention metrics can dangerously obscure customer churn
“Net is a great way to hide both. But expansion, you could be expanding on three accounts that are big and then losing a whole bunch of small ones and it tells you something about the business still. So you need to look at them separately.”
Paul Teshima Sep 10, 2018 ▶ 17:05
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