Selling on Amazon has never stood still.
Every few years, the playbook shifts. New tools appear. Old tactics die. Fees and rules tighten. Competition gets smarter. So it’s easy to look back and think, “It used to be easier.”
Sometimes that’s true. Sometimes it’s nostalgia.
After selling for a good chunk of my life and leaning in through multiple cycles, here’s how I think about the eras of what it means to sell on Amazon, and what each phase rewarded.
Era 0: The Bookseller Era (1999–2007)
This was the original Amazon hustle.
Sellers scanned used books in thrift stores, libraries, garage sales, and estate sales, then flipped them online for huge spreads.
What winning looked like
- $0.50 books sold for $20
- Textbook season felt like printing money
- Rank velocity mattered more than branding
- No FBA, no PPC, and far less competition
What this era created
- The first wave of Amazon entrepreneurs
- Proof that arbitrage could scale
- Early third-party “software needs,” with repricers leading the way
Era 1: The Wild West Era (2007–2013)
This was the era of “just list it.”
There were fewer rules, less competition, and fees that felt almost unreal. If you were early and even slightly competent, you could win.
What winning looked like
- “No rules” energy
- Low competition across many categories
- FBA advantage that made many listings feel unbeatable
The formula
- Be early
- Execute the basics
- Do not overthink it
I started selling around this time. Anything with FBA often dwarfed the competition.
Era 2: The Gold Rush Era (2014–2017)
FBA matured and private label became the mainstream “path.”
It was the peak era of growth hacks. If you knew the game, you could rank products fast.
What winning looked like
- Giveaways and review swaps could rank almost anything
- Alibaba-to-Amazon was a proven model
- Keyword tools moved to center stage
- The ecosystem started to feel real
This is also when events began reflecting the evolution. The first Prosper Show in Salt Lake City was a milestone moment where you could literally see these different seller “eras” showing up in the same room.
Era 3: The PPC and Competition Wars (2018–2020)
Amazon started closing loopholes. The “easy wins” dried up.
Brand building became more important, and advertising became a core skill rather than an optional lever.
What changed
- Amazon killed many of the old ranking hacks
- Brand Registry v2 rolled out
- Amazon Ads went from small to massive, quickly
- Reimbursement tools and advertising tools surged
- Chinese sellers industrialized at scale
What winning looked like
- PPC competence
- Conversion-rate focus
- Catalog discipline
- Brand-level defensibility, not just product-level arbitrage
Era 4: The Aggregator and Saturation Era (2021–2022)
Capital flooded into the market.
Aggregators bought brands at aggressive multiples, and the vibe was: “If it has revenue, it has value.” Then reality hit.
What happened
- Cheap money chased growth
- Brands were bought “with a pulse”
- Supply chains broke
- PPC costs rose fast
- Everyone felt the squeeze at the same time
What winning looked like
- Operational maturity
- Cashflow control
- Supply chain resilience
- Real differentiation that survived rising ad costs
Era 5: The Compliance and Retail Media Era (2023–Now)
Amazon tightened up. Documentation and safety rules became a bigger part of day-to-day operations. Retail media became a cash machine for Amazon, and a requirement for many sellers.
What changed
- More documentation requirements
- More compliance pressure
- Launching products got harder and more expensive
- Ads became less “boost” and more “cost of doing business”
At the same time, social commerce started creating brands out of thin air. TikTok Shop proved you could build demand first, then figure out channels later.
Era 6: The Coming AI Commerce Era (2025–?)
This is the next shift, and it’s already forming.
AI shopping agents will evaluate products for consumers. Discovery may happen outside Amazon more often. And listings will need to be understandable not just to humans, but to machines.
Questions I’m watching closely
- Will AI agents actually replace parts of the buying journey, or just the research?
- Will shoppers move from “ChatGPT research” to “ChatGPT purchase”?
- Will listings need a more machine-readable structure to compete?
- Will Amazon give Rufus capabilities sellers can truly optimize for?
- Who wins the software race as AI becomes the interface?
I just saw a demo of some AI tools (not an agent), and I think SmartScout will be top of mind for some of these use cases. Stay tuned for a launch. I’m genuinely curious to see how these questions play out.
So, Is Selling on Amazon Harder Now?
In many ways, yes:
- Launch costs are higher
- Competition is tighter
- Compliance matters more
- Ads are a bigger part of the equation
But the opportunity never disappears. It relocates.
Every era makes some strategies obsolete, and creates brand-new unfair advantages for sellers who adapt early.
If there’s a timeless lesson across all eras, it’s this: the winners stop trying to relive the old game and start mastering the new one.
