Lessons from $1/day challenge

After 36 days selling something everyday

I planned on selling something for at least $1 for 100 days. But I’m taking a break after succeeding for 36 consecutive days.

It’s freaking hard.

I went in there unprepared, and that didn’t make things easier.

I have a bias toward action. It’s a blessing and a curse. I get impatient and want to move forward as soon as possible. Often, this means presenting half-baked things to people or being in awkward situations where I don’t have everything figured out. But at least it moves the needle, and I’m not stationary.

So here are the lessons I learned while stumbling forward so you can do better than me.

Haggling is a stupid long-term strategy

90% of the time when people tried to haggle, I would stand firm on my price or say, “It’s $XX because of [insert random reason],” and people would pay the price I asked.

If I were you, I’d only haggle if I needed to be more comfortable with rejection. But otherwise, you need to have a serious reason to bring down the price. You can also negotiate on other things than price. Price is just one component of the deal.

People who want to build long-term relationships with you will negotiate properly and ensure everyone is satisfied with the deal. Usually, people will try to make it work and make concessions when it makes sense.

$1 is expensive

Obviously, it’s not that much money. But even your free Notion template might be too costly for some people. It might be 5 clicks away, but it might already be too many clicks for them if they don’t see the value.

I’ve proposed my products or some services for $1, but I’ve been ignored a couple of times. I’m guessing for a few reasons:

• People don’t want or need it.

• It’s too much work even for $1 (think if you need to book something, check your calendar, and enter your credit card info).

• They don’t see the value.

• Lack of credibility (they don’t see why they should listen or talk to me)

• Probably 1000 more reasons.

No products, no money

It sounds trivial, but you won’t make money if you have nothing to sell.

In hindsight, I’d probably prepare a few products before starting a challenge like this one. So I have “ammunitions” and a bunch of things to sell on different mediums. Going into the challenge, I scrambled to find things to sell, and I tried a bunch of random things. But it takes a lot of energy to brainstorm ideas, build the thing, write the promotional content, and post it.

A pricing sweet spot

Lower than $100 sounds like the best compromise for this challenge. Something without fulfilment is even better, like a digital product or access to software. If you make more than one sale per day and need to repeat it the next day, having to fulfill something for a couple of hours will get in the way of selling and promoting.

I feel more than $50-100 is when people start to feel remorse buying, and that’s when impulse buys are lower. Because you’ll start going down random thinking paths when it’s more than $50. What if the product sucks? What if it’s a scam? What if it’s not helpful and a waste of my time and money? Is the guy really an authority in the domain? Are the reviews legit? Etc.

I also feel that around $50 is when it’s more comfortable to use paid advertising because there is more profit margin. If you pay $20 for 100 clicks and only sell a digital product for $15, it’s a big loss because you have fees and taxes and sometimes a bunch of other expenses after that.

Distribution needs to be dialed in

It’s still the goal to make a sale per day eventually. But I’d need to have a system that scales with a heavy emphasis on inbound traffic (SEO and marketplaces) or paid advertising.

Scrambled eggs would feel more organized than my distribution strategy during this challenge.

I just relied on what I had:

• Twitter

• Newsletter

• LinkedIn

• Gumroad customers

I just started promoting to all those channels with varying degrees of success. But it quickly wore off because how many times can you promote the same thing when you run out of excuses? It might be a limiting belief I hold because I’ve seen people promote relentlessly. But I didn’t feel like promoting my stuff like a fisherman at a market.

The closest I had to a good distribution channel was the Facebook Marketplace because there was already a ton of traffic. So, if you have a product in demand, people will contact you. However, this wasn’t scalable because of the limitations of the stuff I wanted to get rid of (I don’t have unlimited quantities of it).

So eventually, the distribution needs to scale, and the products I sell as well. Next time, it would be grandiose to already have a tested and proven distribution channel.

Solid funnels were lacking

In the same vein as the distribution, it would have helped to have a variety of ways to make upsells and to have that dialed in.

With my Upwork course, I set up an upsell to a coaching session, but I could probably have sent emails to people who only purchased the course. Also, if I had a clearer path with a bunch of bigger products once people purchased my smaller ones, it would have helped.

Hard to know what works until you try

After listing dozens of products on the Facebook Marketplace, you get items that receive 20 messages in an hour and some that receive 1 in a month. But it’s hard to know in advance what will have extreme demand and what doesn’t have any.

There needs to be a few simultaneous experiments to have one that takes off, hopefully.

Leverage is awesome

When you get 20 people messaging you, it’s so easy to say no to people who are annoying or flaky. But when you get 1 message every other week, you say yes to the biggest asshole that will haggle like his life depends on it.

In my experience, the biggest leverage is having a sizable emergency fund to rely on, an in-demand skillset and most importantly a working distribution channel. So you know you’ll always have people knocking on the door for your help with dollar bills in their hands.

It takes practice to be comfortable promoting

The most common excuse for people to refrain from promoting or selling their stuff is the fear of appearing “sleazy.”

It’s almost always the same logic. We have a fear of ridicule or feeling shamed, and the rational excuse we come up with is, “I don’t want to be like that sleazy salesman I’ve never met who’s the most extreme example I can imagine based on what I’ve seen in a movie.”

But for each complete crook, there are probably 50 who will never sell, 30 who suck at selling and never listen to your needs, 10 who are good at it, and 10 who are exceptional people trying to help you the best they can.

Anyway, I think there’s still a way to promote without being annoying (chances are you won’t be in 99.9% of cases), and it’s to find good excuses to talk about your stuff. It’s Black Friday, talk about your discount. It’s your birthday, talk about your discount. You launched, talk about your product. You made your first sale, share a link to your product. So on and so forth.

Sometimes, the excuse is simply to have a good story related to the product.

I’m still learning how to do it, but I find it’s the most genuine way for me.

It’s a ton of writing to churn out

There’s the landing page, the social media posts, the email post, the newsletter, the DMs. And it goes on and on and on.

It felt tiring, but in the end, it’s part of the game. I remember seeing this post from Matt Ragland, who wrote 11k words for this promotional strategy. It does take a lot of words which need to be posted on a lot of various places. It’s serious work!

People are sick of sanitized writing

I’ll end with this.

I’ve had so many people reach out to me saying they loved my updates (find them on Twitter) because I was transparent about what I was trying and what was going on.

People are sick of over-sanitized writing which says nothing and doesn’t reveal much about the person. Now, we have AI to write content like that. My general sense is people want more than insights, they want to know the thinking and get a peek of what it feels like to go through those adventures.

That’s my preference as well. I’d rather have people tell me like it is for them (the good and the bad) because it’s more entertaining than reading boring updates as if a project manager was sharing his end-of-week roundup with a manager.

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There are probably more lessons, but that’s it for now. Which lesson resonated the most with you? Let me know :)

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3 juicy links of the week

1. Did My Bestselling Book Turn Out to Be a Financial Failure?

   1. Fascinating read. It’s not because some content has worked before that a different packaging of the same content will be as successful. You can see it clearly. Tiago Forte stopped selling courses and assumed the book would bring new business. But it wasn’t that simple for him and his company. It’s almost always more complex than this, and we need to be careful when placing new bets. Great reminder to take things one step at a time and past success are not a guarantee of future ones!

2. The Stair Step Method of Bootstrapping

   1. Very pragmatic method of building on rented land from Rob Walling. You get inbound sales before completely quitting client work or a job. Most of us would want to tackle the grand idea but would scoff at building something simple that could scale with inbound traffic. Sure, there’s platform risk, but it’s way easier to put yourself in front of the traffic hose rather than building your audience (for example).

3. The ladders of wealth creation: a step-by-step roadmap to building wealth

   1. One of the best breakdowns I’ve seen. You can see that selling services is a big part of learning the ropes before selling products. Selling products is starting on hard mode. But the most important takeaway I get from the article is how each “ladder” is a game with its own rules. When you jump to a new game, you need to learn a whole new set of rules and strategies to succeed. It’s kind of going from social board games you can learn in 5 minutes to proper strategies games with complex rules taking 3 hours to learn with game sessions extending over weeks.