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Jan 17, 2017 · 21m · top-founders

EP 542: HipLead Hits $120k MRR Helping 30 Customers Get More Leads with CEO COnor Lee

Connor Lee · 10m spoken Nathan Latka · 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 episode 542 of The Top Podcast, host Nathan Latka interviews Connor Lee, founder and CEO of HipLead, exploring how the outbound sales acceleration company scaled to $120,000 in monthly recurring revenue across 30 enterprise clients. Connor details his entrepreneurial journey from Y Combinator to building a profitable, 16-person remote business backed by non-dilutive revenue-based financing and exceptional unit economics.

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 46.7% of the talking time here. How this is scored →

Nathan as informed peer 3.9 Guest teaching 2.6 Guest disagreement 1.0 Nathan pushing back 2.3
05100:0010:0020:000:28–4:04 · Nathan as informed peer 4/10 Weekly Podcast Cash Giveaway Announcement Nathan introduces the giveaway and transitions to interviewing Connor about shutting down his previous YC startup Telfi. Nathan presses Connor to avoid giving standard PR answers about shutting down a business gracefully.4:06–8:29 · Nathan as informed peer 6/10 HipLead Core Business Model, Pricing, and MRR Nathan calculates HipLead's MRR based on customer count and price tiers, then delves into co-founder equity vesting schedules and cap table management.8:30–12:11 · Nathan as informed peer 6/10 Revenue-Based Non-Dilutive Debt Financing with Lighter Capital Connor educates Nathan on revenue-based debt financing with Lighter Capital, declining to share exact interest rates while Nathan presses and synthesizes the model for listeners.12:11–14:11 · Nathan as informed peer 5/10 Customer Churn, Acquisition Cost, and Lifetime Value Nathan quickly clarifies whether a 15% churn metric is monthly or annual, and Connor walks through how he calculates a 16k LTV using cohort analysis.14:11–16:49 · Nathan as informed peer 4/10 Historical Growth, Consulting Roots, and Global Remote Team Connor shares HipLead's consulting origin story out of Buyer's Best Friend and details their distributed team structure across the Americas, Europe, and Asia.16:51–19:45 · Nathan as informed peer 2/10 Mid-Roll Feature: The Top Inbox Free Sales Tool Nathan pitches his Top Inbox product and sponsor HostGator before moving through the standard rapid-fire Famous Five questionnaire.19:45–20:32 · Nathan as informed peer 0/10 Episode Recap and HipLead Performance Summary A brief solo outro monologue by Nathan summarizing HipLead's key revenue metrics, team size, and upcoming episode promos.0:28–4:04 · Guest teaching 2/10 Weekly Podcast Cash Giveaway Announcement Nathan introduces the giveaway and transitions to interviewing Connor about shutting down his previous YC startup Telfi. Nathan presses Connor to avoid giving standard PR answers about shutting down a business gracefully.4:06–8:29 · Guest teaching 2/10 HipLead Core Business Model, Pricing, and MRR Nathan calculates HipLead's MRR based on customer count and price tiers, then delves into co-founder equity vesting schedules and cap table management.8:30–12:11 · Guest teaching 6/10 Revenue-Based Non-Dilutive Debt Financing with Lighter Capital Connor educates Nathan on revenue-based debt financing with Lighter Capital, declining to share exact interest rates while Nathan presses and synthesizes the model for listeners.12:11–14:11 · Guest teaching 4/10 Customer Churn, Acquisition Cost, and Lifetime Value Nathan quickly clarifies whether a 15% churn metric is monthly or annual, and Connor walks through how he calculates a 16k LTV using cohort analysis.14:11–16:49 · Guest teaching 3/10 Historical Growth, Consulting Roots, and Global Remote Team Connor shares HipLead's consulting origin story out of Buyer's Best Friend and details their distributed team structure across the Americas, Europe, and Asia.16:51–19:45 · Guest teaching 1/10 Mid-Roll Feature: The Top Inbox Free Sales Tool Nathan pitches his Top Inbox product and sponsor HostGator before moving through the standard rapid-fire Famous Five questionnaire.19:45–20:32 · Guest teaching 0/10 Episode Recap and HipLead Performance Summary A brief solo outro monologue by Nathan summarizing HipLead's key revenue metrics, team size, and upcoming episode promos.0:28–4:04 · Guest disagreement 1/10 Weekly Podcast Cash Giveaway Announcement Nathan introduces the giveaway and transitions to interviewing Connor about shutting down his previous YC startup Telfi. Nathan presses Connor to avoid giving standard PR answers about shutting down a business gracefully.4:06–8:29 · Guest disagreement 1/10 HipLead Core Business Model, Pricing, and MRR Nathan calculates HipLead's MRR based on customer count and price tiers, then delves into co-founder equity vesting schedules and cap table management.8:30–12:11 · Guest disagreement 2/10 Revenue-Based Non-Dilutive Debt Financing with Lighter Capital Connor educates Nathan on revenue-based debt financing with Lighter Capital, declining to share exact interest rates while Nathan presses and synthesizes the model for listeners.12:11–14:11 · Guest disagreement 1/10 Customer Churn, Acquisition Cost, and Lifetime Value Nathan quickly clarifies whether a 15% churn metric is monthly or annual, and Connor walks through how he calculates a 16k LTV using cohort analysis.14:11–16:49 · Guest disagreement 1/10 Historical Growth, Consulting Roots, and Global Remote Team Connor shares HipLead's consulting origin story out of Buyer's Best Friend and details their distributed team structure across the Americas, Europe, and Asia.16:51–19:45 · Guest disagreement 1/10 Mid-Roll Feature: The Top Inbox Free Sales Tool Nathan pitches his Top Inbox product and sponsor HostGator before moving through the standard rapid-fire Famous Five questionnaire.19:45–20:32 · Guest disagreement 0/10 Episode Recap and HipLead Performance Summary A brief solo outro monologue by Nathan summarizing HipLead's key revenue metrics, team size, and upcoming episode promos.0:28–4:04 · Nathan pushing back 3/10 Weekly Podcast Cash Giveaway Announcement Nathan introduces the giveaway and transitions to interviewing Connor about shutting down his previous YC startup Telfi. Nathan presses Connor to avoid giving standard PR answers about shutting down a business gracefully.4:06–8:29 · Nathan pushing back 3/10 HipLead Core Business Model, Pricing, and MRR Nathan calculates HipLead's MRR based on customer count and price tiers, then delves into co-founder equity vesting schedules and cap table management.8:30–12:11 · Nathan pushing back 4/10 Revenue-Based Non-Dilutive Debt Financing with Lighter Capital Connor educates Nathan on revenue-based debt financing with Lighter Capital, declining to share exact interest rates while Nathan presses and synthesizes the model for listeners.12:11–14:11 · Nathan pushing back 3/10 Customer Churn, Acquisition Cost, and Lifetime Value Nathan quickly clarifies whether a 15% churn metric is monthly or annual, and Connor walks through how he calculates a 16k LTV using cohort analysis.14:11–16:49 · Nathan pushing back 2/10 Historical Growth, Consulting Roots, and Global Remote Team Connor shares HipLead's consulting origin story out of Buyer's Best Friend and details their distributed team structure across the Americas, Europe, and Asia.16:51–19:45 · Nathan pushing back 1/10 Mid-Roll Feature: The Top Inbox Free Sales Tool Nathan pitches his Top Inbox product and sponsor HostGator before moving through the standard rapid-fire Famous Five questionnaire.19:45–20:32 · Nathan pushing back 0/10 Episode Recap and HipLead Performance Summary A brief solo outro monologue by Nathan summarizing HipLead's key revenue metrics, team size, and upcoming episode promos.

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

0:00 · Nathan 75.8% · guest 24.2%0:00 · Nathan 75.8% · guest 24.2%3:00 · Nathan 17.1% · guest 82.9%3:00 · Nathan 17.1% · guest 82.9%6:00 · Nathan 36.5% · guest 63.5%6:00 · Nathan 36.5% · guest 63.5%9:00 · Nathan 26.2% · guest 73.8%9:00 · Nathan 26.2% · guest 73.8%12:00 · Nathan 25.9% · guest 74.1%12:00 · Nathan 25.9% · guest 74.1%15:00 · Nathan 54.4% · guest 45.6%15:00 · Nathan 54.4% · guest 45.6%18:00 · Nathan 81.7% · guest 18.3%18:00 · Nathan 81.7% · guest 18.3%21:00 · Nathan 100% · guest 0%21:00 · Nathan 100% · guest 0%
Sharpest disagreement ▶ 9:39 Refusing to disclose interest rate

Connor explicitly pushes back against revealing his proprietary loan terms from Lighter Capital when Nathan asks for the exact interest rate.

 Hardest push from Nathan ▶ 2:37 Pressing beyond startup clichés on shutting down

Nathan interrupts Connor's turtle metaphor to demand the blunt truth about shutting down Telfi without losing face.

 Biggest teaching moment ▶ 9:51 Educating on revenue-based financing mechanics

Connor breaks down how revenue-based debt operates via fixed total interest and bank account auto-deductions rather than monthly compounding interest.

 Nathan holds their own ▶ 10:40 Nathan synthesizes the debt repayment structure

Nathan demonstrates financial acumen by synthesizing the entire loan mechanics into a clear numerical scenario for the audience.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Weekly Podcast Cash Giveaway Announcement 4213 Nathan introduces the giveaway and transitions to interviewing Connor about shutting down his previous YC startup Telfi. Nathan presses Connor to avoid giving standard PR answers about shutting down a business gracefully.
HipLead Core Business Model, Pricing, and MRR 6213 Nathan calculates HipLead's MRR based on customer count and price tiers, then delves into co-founder equity vesting schedules and cap table management.
Revenue-Based Non-Dilutive Debt Financing with Lighter Capital 6624 Connor educates Nathan on revenue-based debt financing with Lighter Capital, declining to share exact interest rates while Nathan presses and synthesizes the model for listeners.
Customer Churn, Acquisition Cost, and Lifetime Value 5413 Nathan quickly clarifies whether a 15% churn metric is monthly or annual, and Connor walks through how he calculates a 16k LTV using cohort analysis.
Historical Growth, Consulting Roots, and Global Remote Team 4312 Connor shares HipLead's consulting origin story out of Buyer's Best Friend and details their distributed team structure across the Americas, Europe, and Asia.
Mid-Roll Feature: The Top Inbox Free Sales Tool 2111 Nathan pitches his Top Inbox product and sponsor HostGator before moving through the standard rapid-fire Famous Five questionnaire.
Episode Recap and HipLead Performance Summary 0000 A brief solo outro monologue by Nathan summarizing HipLead's key revenue metrics, team size, and upcoming episode promos.

Statements from this episode (13)

Assertion Not checkable as stated
Connor Lee's telephony startup Telfi generated a few thousand dollars monthly post-YC
“We were doing a couple thousand dollars a month in revenue we were a couple months out of YC. And the company itself was basically trying to do Google voice for business, compete with grasshopper as a telephony startup that was built on Twilio.”
Connor Lee Jan 17, 2017 ▶ 3:00
Disclosure
HipLead charges $2K-$4K monthly on average; its largest client pays $20K
“And we charge companies between you know, between two and 4000 dollars a month on average. I think our biggest client is around 20,000 dollars a month.”
Connor Lee Jan 17, 2017 ▶ 4:34
Assertion Not checkable as stated
HipLead serves 30 active customers as of late 2016
“We have 30 customers right now.”
Connor Lee Jan 17, 2017 ▶ 4:56
Assertion Not checkable as stated
HipLead generates over $120K in monthly recurring revenue as of late 2016
“Yeah, at least we're doing you know, more than double that.”
Connor Lee Jan 17, 2017 ▶ 5:07
Disclosure
HipLead repurchased unvested equity when Lee's co-founder departed after 18 months
“I've always had, you know, majority ownership of the company. And so you know, he was, you know, co-founder for about a year and a half. And so, you know, basically when he was done, we would, you know, we made sure I started a few companies now and I always m…”
Connor Lee Jan 17, 2017 ▶ 6:25
Disclosure
HipLead used revenue-based financing from Lighter Capital instead of raising equity
“No, it was actually it was actually a loan from lighter capital. Oh, it's sort of like a bank loan. But that it's invoice or revenue financing basically.”
Connor Lee Jan 17, 2017 ▶ 8:49
Disclosure
HipLead raised over $200K in debt financing to make key hires
“It was a little over 200,000 dollars. Okay. It wasn't much. It was just to make a few key hires.”
Connor Lee Jan 17, 2017 ▶ 8:59
Assertion Not checkable as stated
Connor Lee claims HipLead has been profitable since day one
“We've been profitable since day one.”
Connor Lee Jan 17, 2017 ▶ 9:04
Insight
Connor Lee: Revenue-based financing generally requires profitability and $1M ARR
“Usually these types of loans are only available to companies that have, you know, profitable, functional businesses doing, you know, over a million in ARR. I think that's their model.”
Connor Lee Jan 17, 2017 ▶ 11:29
Assertion Not checkable as stated
HipLead's customer acquisition cost is approximately $500
“You know, for us probably close to 500.”
Connor Lee Jan 17, 2017 ▶ 12:58
Assertion Not checkable as stated
HipLead's customer lifetime value reached $16,000 by late 2016
“We're right now at 16,000 dollars.”
Connor Lee Jan 17, 2017 ▶ 13:09
Disclosure
HipLead generated approximately $200K in revenue during its first year
“It was trying to think probably Like 200,000 dollars the first year.”
Connor Lee Jan 17, 2017 ▶ 14:21
Disclosure
HipLead reached just under $1M in annual revenue in 2015
“Yeah, it was just under a million.”
Connor Lee Jan 17, 2017 ▶ 15:42
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