3 ways to monetize
From the least reliable to more control: Affiliates, Sponsorships and Paid Content. If you want an easy way to start getting into the monetization mindset, start with affiliates and sponsorships.
It takes time to find sponsorships but you can get paid for months. That revenue is more consistent than Affiliates for sure.
Look around on Gumroad to find products you like. Approach the seller and ask if they offer an affiliate partnership. Gumroad makes it very easy to add affiliates. You get paid only when someone makes a purchase with your affiliate link. This means it's not regular income
Pete started charging as early as 50 subscribers at around $10. At around 500 subscribers, he charged around $20. At 1K subscribers, he started charging around $50. You can start with as much as 50 subscribers.
Use Business Directories
Look on business directories like Indie Hackers product directory. It lists products with their monthly revenue. Look for those who are making money and if their product category overlaps with your newsletter's audience interests, ask them "would you like to get in front of my audience?"
Build Social Proof
Sponsor other newsletters. Ask them to sponsor you back. Or just trade shout-outs. This shows that there are people interested in sponsoring your newsletters.
Ask your audience
Ask your audience if they or anyone they know are interested in sponsoring your newsletter.
Find sponsors of other newsletters
Companies who are already sponsoring other newsletters already have a budget. Reach out to them and ask if they would be interested in sponsoring you too.
When to monetize?
It's never too early. As long as you have an audience, start monetizing. Pete started as early as 50 subscribers!
Cold Email Tips
Be specific about what your email is about. If your newsletter is relatively new, you don't want your subject to be just that. It has to be enticing to the company you're cold emailing. Pete uses "2000 developers + Stripe" to entice Stripe as 2000 developers is a large number of people that Stripe might be interested in reaching out to.
Pete's first few sponsors were from communities.
1-2-3 Sales Method by Steli Efti steli
The idea Steli shares is to give your prospect 3 problem scenarios. Each of them has to be applicable to their situation / needs. Get them to pick which is most applicable to them. Let them know if they do reply, you'll send them a solution to that problem scenario.
Here's an example Steli provided:
Hey Elon My name is Steli and I'm the CEO at Close. We've realized that most sales managers like yourself often experience one of three problems: 1. You don't have enough leads. 2. You don't have good quality leads. 3. You lack predictability for your funnel. Choose which applies to you and reply with the number. I'll send you something to help fix the problem. Thanks, Steli
Simply brilliant. I'd be obliged to reply to Steli if I received such an email too!
PS: Pete advises against pressure tactics to be ethical. Don't do what you don't want others to do to you! Be nice.