Jun 24, 2017 · 21m · top-founders
700: With $3,000,000 in Projects Completed, Will He Take Down Upwork and Toptal?
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In episode 700 of The Top podcast, host Nathan Latka interviews FreeeUp co-founder Connor Gillivan, detailing how he bootstrapped a high-growth freelance marketplace to millions in transaction volume following his twenty-million-dollar Amazon e-commerce venture.
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 50.8% of the talking time here. How this is scored →
Nathan as informed peer 4.3 Guest teaching 1.8 Guest disagreement 0.8 Nathan pushing back 3.8
speaking balance: gold is Nathan, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 1:54 Connor corrects ownership assumption
Connor firmly clarifies that Portlight is his own operating business rather than a third-party client.
Hardest push from Nathan ▶ 1:17 Challenging top-line Amazon vanity metricsNathan cuts through top-line revenue claims, pushing Connor to disclose real bottom-line profitability.
Biggest teaching moment ▶ 5:07 Differentiating FreeeUp from ToptalConnor educates Nathan on the platform's focus on e-commerce operations rather than high-end developers.
Nathan holds their own ▶ 8:22 Untangling gross merchandise volume and net revenueNathan steps in to dissect the marketplace numbers when Connor conflates weekly processing volume with company take-rate revenue.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Nathan as informed peer | Guest teaching | Guest disagreement | Nathan pushing back | Why |
|---|---|---|---|---|---|---|
| Connor's First Business: Amazon Drop Shipping with Portlight | 6 | 2 | 2 | 7 | Nathan opens with direct skepticism, challenging whether the reported twenty million dollars in Amazon sales translates to real profit. Connor calmly details gross and net margins, clarifying business ownership when Nathan misinterprets. | |
| The Origin and Concept of FreeeUp | 6 | 3 | 1 | 5 | Nathan breaks down FreeeUp's unit economics and take rate, stepping in to untangle weekly gross volume from net platform revenue when Connor mixes up figures. Connor cooperatively clarifies the math. | |
| FreeeUp Growth Channels and Client Onboarding | 5 | 3 | 1 | 6 | Nathan questions the sustainability of FreeeUp's high-touch customer onboarding on small two-dollar initial margins. Connor explains their lifetime customer value strategy and referral mechanics. | |
| Remote Operations and Revenue Trajectory | 6 | 2 | 1 | 4 | Nathan drills into capital allocation, founders' cash payouts, and competitive positioning against incumbents like Upwork and Toptal. Connor outlines their remote team structure and niche focus in e-commerce. | |
| Sponsor Message: Klipfolio Analytics Dashboards | 3 | 1 | 0 | 1 | Following a mid-roll sponsor read, Nathan moves through the standard Famous Five rapid-fire questions, and Connor provides concise answers. | |
| Episode Recap and Farewell | 0 | 0 | 0 | 0 | Nathan summarizes FreeeUp's core metrics, revenue trajectory, and business model in a closing monologue before sharing outro announcements. |
Statements from this episode (12)
Gillivan: Amazon business netted 5% to 10% profit on $20M sales
“So we make about 20 to 30% gross profit margins off of that twenty million dollars in sales. And then usually net profits end up being between five and 10%, depending on how we actually use the gross profits to pay employees and do other things to grow the sto…”
Gillivan: Amazon business generates $1M to $2M annually with 10 freelancers
“So right now, the company still operates. We're doing between one and two million dollars in revenue per year, and we have a team of about 10 people located around the world, just freelancers experts within different aspects of running Amazon stores, who are h…”
Gillivan: FreeeUp focuses on e-commerce and marketing, unlike Toptal
“TopTal is more focused on your higher level developer and designer. Our workers are more specialized within e-commerce business operations, and then also digital marketing.”
Gillivan: FreeeUp has over 500 active billing freelancers
“So we have, right now we have over 500 freelancers in the network who are billing hours on a regular basis.”
Gillivan: FreeeUp averages around $10 per hour across all billing
“It's around 10 dollars per hour right now. I'm pretty sure that's what our average is.”
Gillivan: FreeeUp processes $60,000 to $80,000 weekly in total volume
“We're doing between 60 and 80,000 dollars in revenue per week.”
Gillivan: FreeeUp has 1,500+ signups and 300-500 weekly billing clients
“So we have over 1500 people signed up to the platform now, and then on a weekly basis we're billing between 305 hundred people who are actually using our workers.”
FreeeUp pays clients a 50-cent-per-hour perpetual royalty on referrals
“So a big thing that we do is we have a pretty awesome referral program where our, all of our clients can refer, free up out to their network or out to other people, and they receive 50 cents for every single hour that's billed to anyone that they refer.”
Gillivan: FreeeUp and prior Amazon business are completely bootstrapped
“Totally bootstrapped. Both businesses.”
FreeeUp projects $3M to $4M in 2017 gross volume at 20% take
“That's between three and four top line. So then again, take 20% of that, and they'll give you what the company's actually earning.”
FreeeUp pays 50% of earnings to founders, reinvesting only 25%
“For any of that 20% that we're earning we usually take about half of it and pay ourselves out, put another quarter of it into actually regrowing the company, and then put the rest of the quarter into kind of a cash reserve so that we can make sure that the com…”