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Aug 17, 2021 · 18m · top-founders

He's Beating Cancer While Building Fintech Health Tool, $1.6m ARR Bootstrapped

Greg Phillips · 12m spoken Nathan Latka · 3m spoken Frank Bien · 4s spoken Eric Yuan · 4s spoken Vivek Bhaskaran · 2s 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, Cover Me founder and CEO Greg Phillips discusses bootstrapping his AI-driven healthcare fintech platform to $1.6 million ARR while overcoming cancer, detailing his enterprise sales structure, unit economics, and upcoming Series A fundraising plans.

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 23.7% of the talking time here. How this is scored →

Nathan as informed peer 3.2 Guest teaching 1.4 Guest disagreement 0.0 Nathan pushing back 1.0
05100:0010:000:26–3:12 · Nathan as informed peer 1/10 Show Announcement and Subscription Platform Pitch The segment begins with a promotional platform pitch and ad read before Nathan introduces Greg. Greg shares his personal background with cancer and the motivation behind launching Cover Me without any friction.3:15–7:13 · Nathan as informed peer 3/10 How Cover Me Discovers Healthcare Payment Solutions Nathan inquires into payment mechanisms, historical bootstrap capital ($800k), and equity splits. Greg candidly describes his entrepreneurial background and previous ventures.7:14–10:58 · Nathan as informed peer 5/10 Team Structure, Quota Targets, and Sales Compensation Nathan drills into sales commission structures, quota expectations, and performs real-time ARR to MRR conversions. Greg shares details about company growth while dealing with cancer treatment.10:59–13:17 · Nathan as informed peer 4/10 Bootstrapping Strategy, Credit Facilities, and Series A Plans Nathan asks about debt facilities and upcoming Series A round parameters. Greg discusses taking a $125k credit line and considering raising $4M-$5M at a $12M pre-money valuation.13:18–14:54 · Nathan as informed peer 3/10 Customer Breakdown, Unit Economics, and Pricing Adjustments Nathan prompts for client breakdown and ACVs across the 36 customers. Greg details the variance between nursing home contracts and hospital contracts, highlighting plans to raise rates.0:26–3:12 · Guest teaching 1/10 Show Announcement and Subscription Platform Pitch The segment begins with a promotional platform pitch and ad read before Nathan introduces Greg. Greg shares his personal background with cancer and the motivation behind launching Cover Me without any friction.3:15–7:13 · Guest teaching 2/10 How Cover Me Discovers Healthcare Payment Solutions Nathan inquires into payment mechanisms, historical bootstrap capital ($800k), and equity splits. Greg candidly describes his entrepreneurial background and previous ventures.7:14–10:58 · Guest teaching 1/10 Team Structure, Quota Targets, and Sales Compensation Nathan drills into sales commission structures, quota expectations, and performs real-time ARR to MRR conversions. Greg shares details about company growth while dealing with cancer treatment.10:59–13:17 · Guest teaching 1/10 Bootstrapping Strategy, Credit Facilities, and Series A Plans Nathan asks about debt facilities and upcoming Series A round parameters. Greg discusses taking a $125k credit line and considering raising $4M-$5M at a $12M pre-money valuation.13:18–14:54 · Guest teaching 2/10 Customer Breakdown, Unit Economics, and Pricing Adjustments Nathan prompts for client breakdown and ACVs across the 36 customers. Greg details the variance between nursing home contracts and hospital contracts, highlighting plans to raise rates.0:26–3:12 · Guest disagreement 0/10 Show Announcement and Subscription Platform Pitch The segment begins with a promotional platform pitch and ad read before Nathan introduces Greg. Greg shares his personal background with cancer and the motivation behind launching Cover Me without any friction.3:15–7:13 · Guest disagreement 0/10 How Cover Me Discovers Healthcare Payment Solutions Nathan inquires into payment mechanisms, historical bootstrap capital ($800k), and equity splits. Greg candidly describes his entrepreneurial background and previous ventures.7:14–10:58 · Guest disagreement 0/10 Team Structure, Quota Targets, and Sales Compensation Nathan drills into sales commission structures, quota expectations, and performs real-time ARR to MRR conversions. Greg shares details about company growth while dealing with cancer treatment.10:59–13:17 · Guest disagreement 0/10 Bootstrapping Strategy, Credit Facilities, and Series A Plans Nathan asks about debt facilities and upcoming Series A round parameters. Greg discusses taking a $125k credit line and considering raising $4M-$5M at a $12M pre-money valuation.13:18–14:54 · Guest disagreement 0/10 Customer Breakdown, Unit Economics, and Pricing Adjustments Nathan prompts for client breakdown and ACVs across the 36 customers. Greg details the variance between nursing home contracts and hospital contracts, highlighting plans to raise rates.0:26–3:12 · Nathan pushing back 0/10 Show Announcement and Subscription Platform Pitch The segment begins with a promotional platform pitch and ad read before Nathan introduces Greg. Greg shares his personal background with cancer and the motivation behind launching Cover Me without any friction.3:15–7:13 · Nathan pushing back 1/10 How Cover Me Discovers Healthcare Payment Solutions Nathan inquires into payment mechanisms, historical bootstrap capital ($800k), and equity splits. Greg candidly describes his entrepreneurial background and previous ventures.7:14–10:58 · Nathan pushing back 2/10 Team Structure, Quota Targets, and Sales Compensation Nathan drills into sales commission structures, quota expectations, and performs real-time ARR to MRR conversions. Greg shares details about company growth while dealing with cancer treatment.10:59–13:17 · Nathan pushing back 1/10 Bootstrapping Strategy, Credit Facilities, and Series A Plans Nathan asks about debt facilities and upcoming Series A round parameters. Greg discusses taking a $125k credit line and considering raising $4M-$5M at a $12M pre-money valuation.13:18–14:54 · Nathan pushing back 1/10 Customer Breakdown, Unit Economics, and Pricing Adjustments Nathan prompts for client breakdown and ACVs across the 36 customers. Greg details the variance between nursing home contracts and hospital contracts, highlighting plans to raise rates.

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

0:00 · Nathan 50.9% · guest 49.1%0:00 · Nathan 50.9% · guest 49.1%3:00 · Nathan 6.3% · guest 93.7%3:00 · Nathan 6.3% · guest 93.7%6:00 · Nathan 22.2% · guest 77.8%6:00 · Nathan 22.2% · guest 77.8%9:00 · Nathan 11.7% · guest 88.3%9:00 · Nathan 11.7% · guest 88.3%12:00 · Nathan 11.1% · guest 88.9%12:00 · Nathan 11.1% · guest 88.9%15:00 · Nathan 39.6% · guest 60.4%15:00 · Nathan 39.6% · guest 60.4%18:00 · Nathan 0% · guest 0%18:00 · Nathan 0% · guest 0%
Sharpest disagreement ▶ 13:22 Gentle correction on customer market segmentation

In a very collegial interview, Greg offers his mildest pushback by clarifying that their 36 customers are divided between distinct nursing home and hospital segments rather than just hospitals.

 Hardest push from Nathan ▶ 8:55 Clarifying ARR versus total monthly recurring revenue

Nathan cuts through the ambiguous addition of $270k ARR to pin down the exact current baseline MRR.

 Biggest teaching moment ▶ 3:18 Educating on real-time healthcare financing mechanisms

Greg outlines the ecosystem of hospital financial assistance programs, government programs, and commercial lending options that hospital patients typically struggle to navigate.

 Nathan holds their own ▶ 8:57 Instant MRR mental math and pipeline deconstruction

Nathan swiftly recalculates the guest's reported ARR gain into $22.5k incremental MRR and presses for the actual net monthly total.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Show Announcement and Subscription Platform Pitch 1100 The segment begins with a promotional platform pitch and ad read before Nathan introduces Greg. Greg shares his personal background with cancer and the motivation behind launching Cover Me without any friction.
How Cover Me Discovers Healthcare Payment Solutions 3201 Nathan inquires into payment mechanisms, historical bootstrap capital ($800k), and equity splits. Greg candidly describes his entrepreneurial background and previous ventures.
Team Structure, Quota Targets, and Sales Compensation 5102 Nathan drills into sales commission structures, quota expectations, and performs real-time ARR to MRR conversions. Greg shares details about company growth while dealing with cancer treatment.
Bootstrapping Strategy, Credit Facilities, and Series A Plans 4101 Nathan asks about debt facilities and upcoming Series A round parameters. Greg discusses taking a $125k credit line and considering raising $4M-$5M at a $12M pre-money valuation.
Customer Breakdown, Unit Economics, and Pricing Adjustments 3201 Nathan prompts for client breakdown and ACVs across the 36 customers. Greg details the variance between nursing home contracts and hospital contracts, highlighting plans to raise rates.

Statements from this episode (11)

Disclosure
Phillips: Cover Me founders invested about $800,000 of personal capital
“We put in about 800,000 total.”
Greg Phillips Aug 17, 2021 ▶ 5:24
Disclosure
Phillips: Cover Me founder owns majority equity with two co-founders
“No, I own a little bit more than a majority, and my two co-founders own the rest.”
Greg Phillips Aug 17, 2021 ▶ 6:12
Prediction Not checkable as stated
Phillips: Cover Me will reach about $1.6 million in revenue in 2021
“This year we will finish the year at about one six.”
Greg Phillips Aug 17, 2021 ▶ 7:11
Disclosure
Cover Me Pays Sales Reps $100K Base Plus 10% Commission
“We pay them a 100,000 as a base, and then 10% on their first year, on the first year of the revenue, and then there's some residuals.”
Greg Phillips Aug 17, 2021 ▶ 8:30
Assertion Not checkable as stated
Phillips: Cover Me added three customers and $270K in ARR last month
“We just added three new customers. So we added two point, or excuse me, 270,000 in revenue last month.”
Greg Phillips Aug 17, 2021 ▶ 8:45
Assertion Not checkable as stated
Phillips: Cover Me's monthly revenue dipped to about $100K during COVID
“Oh, we struggled a little bit last year. We dipped all the way down when we were dragging around about a hundred a month.”
Greg Phillips Aug 17, 2021 ▶ 9:15
Opinion
Phillips: Cover Me needs $4M to $5M to scale properly
“You know, to scale this thing and do it right, I think we need four or five million.”
Greg Phillips Aug 17, 2021 ▶ 12:28
Opinion
Phillips targets roughly $12M valuation for Cover Me
“Well we, we're sitting down to talk about this here in about a month or so, but, you know, I think we're probably realistically looking at maybe, maybe one point maybe twelve million.”
Greg Phillips Aug 17, 2021 ▶ 12:39
Assertion Not checkable as stated
Phillips: Cover Me has 36 total customers
“36 total.”
Greg Phillips Aug 17, 2021 ▶ 13:22
Opinion
Phillips: Cover Me prices its products 50% beneath market rates
“We think we're about 50% beneath the market on both of them.”
Greg Phillips Aug 17, 2021 ▶ 14:37
Prediction Not checkable as stated
Phillips: Personal angel investment Rehinged will be a marketing AI superstar
“And in fact, I just invested some of my own money into that deal. Rehinged is going to be a superstar in that space.”
Greg Phillips Aug 17, 2021 ▶ 16:19
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