Losing money intentionally to win loyalty

Notes from James:

I wish I had been Kolin Jones when I was 18 years old.

When Colin was 19, during COVID, he set up his own private jet brokerage out of a college dorm room. No investors. No jets. No connections. Just a GoDaddy website, an email address, and an obsessive willingness to send 2,500 cold emails a day.

Amalfi Jets is on track to do $120 million in revenue this year. And he still doesn't own a single plane.

I love how he thought about competition. He literally calculated: my competitor sends 400 emails a day, I'll send 2,500 — that means I'm doing six of his days in one of mine. Do that for a month and I'm four months ahead. That was the whole strategy at the start. Beautiful.

And then TikTok changed everything. One video about a client who chartered two jets — one for his wife, one for his mistress — got a million views. 150,000 people hit their website. 15,000 flight requests in a single day. The entire trajectory of the company shifted because of a free video.

He also talked about losing money on purpose on his first sale — selling a $24,500 flight for $20,000 to lock in loyalty. Pure Amazon thinking. I love that.

And there's a story about a client stranded on the Galapagos Islands whose plane broke down. The client's assistant asked about bribing customs officials. Listen for how Kolin handled it.

This is a great template if you're an entrepreneur, a creative, or anyone trying to build something from nothing. Please listen.

Episode description:

Kolin Jones was 19 years old, in his college dorm during COVID, when he noticed something: commercial flights were grounded, but private jets were surging. He got his pilot's license at Van Nuys Airport — the busiest private jet airport in the world — and launched Amalfi Jets with nothing more than a website, a cold email strategy, and a plan to out-hustle every competitor through sheer volume.

James and Kolin break down exactly how the private jet charter brokerage model works, why you can legally set one up today with zero certification or licensing, why Amalfi turns down roughly $1M/week in deals over safety concerns, and what separates a legitimate broker from the hundreds of unregulated players flooding the market. They also get into the social media strategy that transformed the company — why Kolin was initially against TikTok, what changed his mind, and how one viral video created 15,000 flight requests in a day.

Plus: what it actually costs to own a private jet, the real economics of flying private vs. first class, why the richest clients show up in jeans and an Uber, what happens when a client punches the pilot mid-flight, and the watch Kolin bought himself the first month Amalfi crossed $2M in revenue.

What you'll learn

• How a private jet charter brokerage works — and why it requires zero licensing or certification to start
• The cold email strategy Kolin used to out-hustle every competitor from his college dorm
• Why Kolin intentionally lost money on his first few sales — and why it paid off
• The real cost of owning a private jet (it's about $800K/year just to park it)
• Why Amalfi turns down ~$1M/week in business due to safety and legal concerns
• How one TikTok about a client's mistress generated 150,000 website visitors and 15,000 flight requests in a single day
• Why Kolin tracks which shirt color makes his videos go more viral (black = +36%)
• When flying private is actually cheaper than first class — and the math behind it
• The Galapagos breakdown story: a stranded client, a broken jet, and a customs bribe request
• What ultra-high-net-worth clients actually look like vs. the Instagram version
• Kolin's plans for Amalfi: acquisitions, possible PE partnership, and why he won't go public

Timestamps:

00:00 Why flying private ruins you for commercial forever

06:00 What Amalfi Jets actually is — and how the charter brokerage model works

09:00 The real cost of owning a private jet

13:00 The wild west of jet brokerage — zero regulation, zero licensing required

16:00 The Galapagos story: broken jet, stranded client, and a near-bribe

20:00 Colin's origin story: COVID, flight school, and cold emailing 2,500 people a day

26:30 The first sale: losing $4,000 on purpose and the Amazon strategy that built loyalty

30:00 How one TikTok about a mistress changed everything36:00Inside Amalfi's content machine — and the clients who punch pilots

41:00 When private is actually cheaper than first class — the real math

46:00 The tech behind Amalfi: AI fleet optimization, 72K-member app, and social listening

50:00 Burying competitors with relevance — and what's next for Amalfi5

7:00 The first splurge: an Omega Seamaster and what it represents

Additional Resources:

• Amalfi Jets
• Kolin's Instagram
• Kolin on TikTok
• Amalfi Jets on TikTok

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