Why Marketing Is So Hard For First-Time Entrepreneurs

Hey Everyone!

I thought I’d share my little attempt at trying to “get to the core” of something that seems to plague the majority of us bootstrappers and entrepreneurs - that dreaded nemesis of ours known as “marketing”.

In essence, I’m trying to get as many bootstrappers and internet entrepreneurs as possible to share their experiences about marketing - about what’s worked - and especially about what hasn’t - and to share that information with as many people as possible.

I wrote a post about the trials and tribulations about marketing as a first-time entrepreneur here that you’re more than welcome to check out:


Or, if you just want to get to the goodies, this is the Google Form I’m hoping to get people to use to share their experiences through:

All submissions will remain anonymous unless otherwise noted, and my intent is to turn this into a full, useful summary and synopsis that first-time entrepreneurs can use to help sift through the B.S. that seems to permeate the internet marketing landscape.

I’d appreciate any insights that any of you have, and hope that you’ll contribute to (what I hope) will be something that can help steer others away from “bad” marketing and towards resources and tactics that actually garner real-world results.




Not only for first-timers. I think it’s more about how much you like marketing and how easy your niche is. On my last 3 products before current one, I’ve done 0 marketing and got tons of customers just because there were many tight communities and 2 out of 3 I was the first on the market, which is a huge advantage.

On more mature markets like I’m now, it’s much harder, even with a great product.


I think the #1 problem is not playing customer.

After 20 successful years, I started doing live demos and have found TONS of things that could be better and EASILY fixed. Simple wording issues, etc.

It’s easy to think that you know is in the customer’s mind. And it’s even easier to be wrong.


Thanks @Clay_Nichols - This is an excellent point!

On more mature markets like I’m now, it’s much harder, even with a great product.

Agreed. Definitely much more effort is involved.

On my last 3 products before current one, I’ve done 0 marketing and got tons of customers just because there were many tight communities and 2 out of 3 I was the first on the market, which is a huge advantage.

Curious what kind of niches you targeted with these? That’s like the average bootstrapper’s dream right there :slight_smile: Good for you!

One thing I’ve learned recently (in the last few years) is how hard it is to get good information from a Survey for several reasons:

  1. Are survey questions aren’t as clear as we think they are. (try TESTING your Survey with 5 people first. You maybe surprised at how folks misinterpret questions)
  2. Surveys are awful for finding WHATs and WHYs like user needs. They are useful only for COUNTING things. Users don’t normally know WHAT they need. You need open ended questions to get to the WHATs. Then when you find the WHATS, you can COUNT them with Surveys.
    If you haven’t confirmed that a small test batch of folks have the WHAT or WHY, then your Survey likely does not ask the right WHAT’s or WHYs.

@Clay_Nichols I could not agree more. There is a big dichotomy between what users say they want and what they actually do. For these precise reasons many mature product companies do extensive “user testing”. There is a whole class of SaaS products that allow you do to this specifically for user/usability testing. However, what do you think about extending on this idea to look at how users actually perform certain task. So instead of asking “survey questions” wouldn’t it be better if we give them general task-based instructions and watch how they perform these tasks ( in the form of a recorded screen capture with audio) ?

For example, instead of asking survey questions about produce delivery, give them a short task:

“Go to Google.com, find some organic produce, and get it delivered to your home. Please think out as your perform this activity”.

It all depends on what your goal is.

I see several goals starting with:

  1. What is your PAIN (What Customers Want is a GREAT book on this. ).
  2. What are users desired OUTCOMES (a change in a metric in a direction. So “fewer clicks to launch new template”, etc.). It would be good to watch them to find out what those OUTCOMES are. the above book recommends talking to 150 customer mimimum asking very open ended question.
  3. Once you ID the OUTCOME , THEN you get to Usability of your solution. (And this is where you’d do an MVP mockup)

I’m working on #3. And YES, you’re right, I give them a Script (see What Customers Want , GREAT book on UX) for examples JUST like what you mentioned: give’m a back story and a goal. And then watch 'em.

Usability Testing TRICK:
Do testing (with fresh eyes) on COMPETITORS website first.
Softens the blow when you find UX Nightmare on UR site.

Usability and improving conversion rate it’s super important, but what I think that’s the biggest issue for first-time entrepreneurs is getting traffic first, and quality one.

If you don’t get users and traffic, you can tweak as much as you want because not enough people will be affected to even measure the results.

I had a landing page optimization tool, like Optimizely by for landing pages only, and some people started doing A/B testing and stuff like that when they had lower 100 visitors/days. It doesn’t work like that.

The first, most important issue is getting traffic. Once you have that, you can start working on usability, A/B testing, etc


A/B testing is seductive and appealing to engineers. But the reality is that you need a very large sample size unless you’re getting a dramatic (very statistically significant) change.


As well as testing your questions with people, watch Yes Minister on leading questions for inspiration :wink:

Then, after that, ask friends to wilfully misinterpret your questions.

Its like an exercise we did in the Founder Institute for choosing business names - give people a candidate name and ask them what they don’t like about it.