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The Pains of Making Craigslist a Side-Hustle, and How We Think Tech Can Help

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A little over a year ago, a friend of mine was purchasing a car for college on Craigslist. When he finally came across the right car for the right price — and after a cumbersome exchange with the seller — my friend headed to the seller’s house to complete the transaction. Parked in the seller’s driveway and along the street were six vehicles, and the seller walked out of his duplex glued to his phone as notifications poured in. His wife stayed inside, trying to control two screaming toddlers.

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After finalizing some paperwork at a local dealership, my friend offered to give the seller a ride home, and on the way inquired about the seller’s Craigslist business. The notifications flooding his screen were texts from potential buyers, and the seller could hardly keep track of his conversations, nonetheless hold personal text conversations alongside his business ones. It finally made sense to my friend why after every text it seemed like the seller forgot what the conversation was about…

Building a side-business is hard. If it wasn’t already hard to find enough hours in the day, running a business on just a few hours every evening is a time management disaster. What makes the “Craigslist side-hustle” so challenging, and how can technology help? Two friends (including the one I’ve been talking about) and I started working nearly 8 months ago to figure it out. Here’s where we’re at:

The Pains

Want to starting flipping on Craigslist? These are the things we’ve determined will inevitably drive you crazy:

1. Scams or slow communication. Pick your poison!

I shouldn’t need to tell you that posting a personal phone number on a public listing as a point of contact is risky business (ever heard of a port-out scam?), but you’d be surprised how many Craigslist sellers fall into the trap out of necessity. Craigslist itself, not known as the most responsive to feature-requests, has implemented a two-way email relay system to address seller security concerns. Yet, the system comes with its quirks, not to mention inherent inefficiency. The email system is often described as “annoying” to use, especially on a mobile device, and has difficulty passing along simple images and other attachments at times. Plus, email is slow. Frequent sellers want their product out the door as soon as possible, and email communication just doesn’t beat text or a good old-fashioned phone call. So we’re back to square one; Contact via a cell phone is clearly easier and faster, but not safe. What if sellers could communicate easily, quickly, AND safely?

2. Spam. Lots of it.

Regardless of whether you decide to use your personal phone number or email, you’re going to get a lot of messages you just don’t care about. Bots can potentially get hold of your contact information, and you’ll frequently get random, unsolicited messages totally unrelated to your listings. Also responding to redundant buyer questions can be a huge time sink, especially when answering “Yes” to “Is this item still available?” at the beginning of every conversation. Finally, that Craigslist car salesman I was talking about earlier would probably tell you that managing your Craigslist communication with multiple live listings — while still keeping tabs on your personal communication — can get pretty overwhelming. What if sellers could manage their business communication efficiently and independently of their personal communication, all while automatically ignoring spam?

3. Doing business with buyers you probably shouldn’t do business with.

It’s no fault of your own, Craigslist just doesn’t help you distinguish the good buyers and sellers from the bad (ie. Ebay’s super-helpful buyer/seller quality ratings). We’ve heard some pretty crazy stores that you’ve probably heard too: Buyer meets seller and offers half of the decided price because he/she “forgot the rest at home”. Buyer asks twelve questions about an item over text before low-balling and offering a third of the asking price. Buyer and seller agree to meet and the buyer just doesn’t show up. Buyer asks seller to meet in a random motel 20 miles outside city limits to complete a transaction… What if sellers could spend less time dealing with these buyers and more time with the good ones?

Obviously, there are quite a few problems that Craigslist hustlers face, and the ideal solution would address these while being easy-to-use and cheap. Craigslist sellers simply don’t have time to integrate technology that isn’t dead-simple into their workflow, and anything too expensive can only hurt the bottom line of sellers who already have small margins.

The Solution

Enter, Pradl. Pradl is the result of the team’s desire to tackle these issues and improve the experience of thousands of Craigslist sellers. We believe being open about our ideas for solving these problems gives us the best chance to validate and improve them, and therefore I’d like to share how the team at Pradl believes chatbots can provide a cohesive solution that Craigslist hustlers need.

A Business Phone Number That’s More Than Just a Burner

Our initial takeaway was that Craigslist sellers need the speed and mobility of SMS with a layer of security between their number and their public listings, and we jumped to the conclusion that burner phone numbers meet these two demands. Yet, the solution is not as obvious as it seems. Having a secondary phone number is great for protecting your personal one, and it technically isolates business and personal text messages, but that’s about it. At the end of the day, a secondary phone number won’t help manage spam and unsolicited contact, won’t get rid of redundant buyer questions, and it certainly won’t help to keep bad buyers away from your listings. Craigslist hustlers need more than just a burner number.

The Vision

Ultimately, the core, pervasive problem underlying the previously stated concerns is the lack of a filter. As humans, we can naturally discern relevant questions from irrelevant ones, and can pick up on context in conversations that would suggest the intent of a person on the other end. Of course, it has traditionally been up to Craigslist sellers to make these decisions regarding conversation filtering on their own. It is up to the seller to filter out spam messages and unsolicited communication. The seller has to wade through redundant buyer questions to get to the task at hand: selling a product. The seller has to determine the reliability of a buyer, and must make a decision to sell accordingly. The team examined this core problem, and we asked ourselves: “How can we build a product that can make these decisions accurately so that the seller doesn’t have to?”.

In the current stage of our product the solution is much more cutthroat than the vision, but we continue to ask this question to maintain focus as Pradl becomes more advanced.

CAPTCHA Security, Automatic Answering, and Buyer Dependability Analysis

We have a lot of ideas about how we can answer the question above, but here’s some of the stuff we’re working on: When the buyer contacts a Pradl number on a sellers listing, they are asked to authenticate that they’re human through a text-based CAPTCHA. That’s a simple but effective solution to eliminating bot-spam entirely. Next, buyers are told that they can ask questions about the listing. Pradl is able to understand the details of a listing and answer questions about an item accordingly that would be “redundant” for a seller otherwise. If Pradl can’t answer a question, it proceeds to ask the buyer some screening questions that the seller chooses before passing them off to the seller, like “Are you willing to meet in X area?”, or “Is your offer above Y minimum price?”. We believe that having a chatbot ask these questions can do a lot to prevent bad buyers from ever deciding to buy from Pradl sellers; Bad buyers would rather find an easier target.

From there, the seller can choose whether or not to contact the buyer with their actual phone number based on Pradl’s conversation, which they can view through a link we automatically text to them. Another metric a seller can use for deciding whether or not to respond to an authenticated buyer is the Buyer Dependability Rating, which works similar to Ebay’s system. When a transaction goes smoothly for a Pradl seller, the buyer’s number is associated with a rating that responds accordingly. Likewise, sellers can report buyers by phone number when a transaction doesn’t go well. Many bad buyers often work around a bad rating by creating another email, but because our system saves buyer ratings by phone number it’s more difficult and more costly for buyers to obfuscate a bad transaction history. Any Pradl seller that comes into contact with that buyer’s number in the future sees their rating.


Craigslist hustlers face a lot of annoying problems, and one of the reasons the team and I feel passionate about addressing them is the overall lack of attention they receive. Some of the best technologies and many of the greatest companies found success through tackling problems that nobody thought possible to solve, and although fiddling with buyer and seller interaction seems like a daunting task, we believe that technology — specifically chatbot tech — has a real opportunity here to meet a genuine need.

This article was quite the brain dump, but, again, this is primarily intended to generate discussion and invite criticism. You can email me at [email protected].

Thanks for reading, stay tuned for more updates about Pradl.

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