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Derek Sivers vs Sahil Lavingia

Products, revenue & stack compared side by side.

Derek Sivers avatar

Derek Sivers

Musician who accidentally built CD Baby, sold it for $22M, and writes books on how to live

Sahil Lavingia avatar

Sahil Lavingia

Founder of Gumroad and author of The Minimalist Entrepreneur

Derek Sivers vs Sahil Lavingia at a glance

Derek Sivers and Sahil Lavingia are both indie makers listed on IndieMakerList. They overlap in Creators & Writers, E-commerce and Educators & Course Creators. Derek is based in New Zealand, Sahil in Brooklyn, United States. Derek started in 1997 and Sahil in 2011. Derek Sivers has 3 products listed on IndieMakerList vs Sahil Lavingia's 3. Derek has sold 2 products. Sahil self-reports $17.8M/yr (Gumroad, 2025); Derek hasn't shared a revenue figure publicly. On X, Derek has about 286K followers and Sahil about 394K.

Side-by-side comparison

Based in
Derek Sivers: New Zealand
Sahil Lavingia: Brooklyn, United States
Started
Derek Sivers: 1997 (29 yrs indie)
Sahil Lavingia: 2011 (15 yrs indie)
Revenue (self-reported)
Derek Sivers: Not public
Sahil Lavingia: $17.8M/yr (Gumroad, 2025)self-reported, as of 2025 · source for Sahil Lavingia's revenue
Products listed
Derek Sivers: 3
Sahil Lavingia: 3
Product status
Derek Sivers: 0 active · 2 acquired · 1 shut down
Sahil Lavingia: 3 active
X followers
Derek Sivers: 286K
Sahil Lavingia: 394K
Style
Derek Sivers: solobootstrappedexited
Sahil Lavingia: builds in public
Courses & resources
Derek Sivers: 6
Sahil Lavingia: 1

Revenue figures are self-reported by each maker and not audited; dates and scope differ. Highlighted categories are shared by both.

Top products

Derek Sivers avatarDerek Sivers

CD Baby logo

CD Baby

cdbaby.com

acquired

Online store and distributor for independent musicians; became the largest seller of independent music online. Sold in 2008 for $22M.

HostBaby logo

HostBaby

hostbaby.com

acquired

Web hosting for musicians, sold together with CD Baby in 2008.

W

Wood Egg

sive.rs

shutdown

Project to publish yearly entrepreneurship guidebooks on 16 Asian countries, started while living in Singapore.

Sahil Lavingia avatarSahil Lavingia

Gumroad logo

Gumroad

gumroad.com

Platform for creators to sell digital products, memberships and courses directly to their audience.

$17.8M in 2025TrustMRR ↗
Flexile logo

Flexile

flexile.com

Open-source tool for paying contractors and managing equity, spun out of how Gumroad runs its team.

Helper logo

Helper

helper.ai

Open-source AI-powered customer support tool from the Antiwork family.

Tech stack

No tools in common in their publicly listed stacks. See the indie maker tech stack.

Derek Sivers avatarDerek Sivers

RubyPostgreSQLOpenBSDVim

Sahil Lavingia avatarSahil Lavingia

No stack shared publicly.

How they build

Derek Sivers avatarDerek Sivers

  • Hell yeah or no: if you're not wildly excited about something, say no.
  • Business is about serving people, not chasing growth; make it a utopia for your customers.
  • Don't need money? Then optimize for freedom and learning instead.
  • Start tiny and stay focused on one thing at a time.
  • Be tech-independent — prefer open, self-hosted tools you control.

Sahil Lavingia avatarSahil Lavingia

  • Start with a community you are already part of, then build for it.
  • Do things manually before you build software, and build as little as possible.
  • Profitability gives you the freedom to make your own decisions.
  • Run the company in public: open metrics, open board meetings, open source.
  • Creators should own their audience and get paid directly.

Learn from Derek and Sahil

Derek Sivers vs Sahil Lavingia FAQ

Who makes more money, Derek Sivers or Sahil Lavingia?

Sahil Lavingia self-reports $17.8M/yr (Gumroad, 2025). Derek Sivers' revenue is not public, so a direct comparison isn't possible.

Who has built more products, Derek Sivers or Sahil Lavingia?

Derek Sivers has 3 products listed (CD Baby, HostBaby and Wood Egg); Sahil Lavingia has 3 products listed (Gumroad, Flexile and Helper).

What tech stack do Derek Sivers and Sahil Lavingia use?

Derek Sivers uses Ruby, PostgreSQL, OpenBSD and Vim. Sahil Lavingia hasn't shared a stack. They don't list any tools in common.

Where are Derek Sivers and Sahil Lavingia based?

Derek Sivers: New Zealand. Sahil Lavingia: Brooklyn, United States.

Who has been an indie maker longer, Derek Sivers or Sahil Lavingia?

Derek Sivers started in 1997 (29 years indie); Sahil Lavingia started in 2011 (15 years indie).

Are Derek Sivers and Sahil Lavingia bootstrapped?

Derek Sivers is listed as bootstrapped; Sahil Lavingia isn't tagged as bootstrapped on IndieMakerList.

Full profiles

Read the full story, timeline and links on Derek Sivers's profile and Sahil Lavingia's profile.

More comparisons