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Hi, I'm Bobby Matson.

I'm a NYC-based software engineer and entrepreneur. I love working on new business models and experimenting with funky ideas. Shoot me an email if you'd like to collaborate on one!

Bobby's Blog

Getting to the Root

Understanding someone else’s problems is super hard.

We can hear what’s being told to us, but still not grasp the underlying root problems.


Last week, I talked a bit about an approach to discovering customers, which involved interviewing a bunch of folks about their issues surrounding debt. After each interview, I relistened to the recording to understand what had really been discussed.

What were the real pains? What were the common threads in each of these discussions?

I was getting a clearer picture of how people approached debt, but it was still foggy. I needed a more detailed viewpoint since there’s so much consumer pain related to debt.

New Perspective

5 Whys

Enter the 5 Whys!

5 Whys is an exercise where you propose a problem and simply ask “why?”.

Usually, you’ll have more than one answer to the question. From there, you continue asking “why?” for each answer, until you’ve asked “why” 5 times for each problem.

Root problems end up looking quite different than the surface issues. An example chain:

I have stomach pain


I’m hungover


I drank too much last night


I did those shots at the end of the night


I have trouble saying no to friends

Aha! Maybe a little discipline and more confidence saying no would lead to less future stomach pain? ;)

I did this same thing for my pain points. For each broad assumption, I drew a tree five levels deep.

People have anxiety about loan payments

5 Whys

People have no visibility into the cost of debt

5 Whys Again

I started seeing much clearer problem sets. Some examples:

  • Risks are more expensive with too much debt. The more debt we take, the less we have control of our destiny.
  • We don’t make enough income. Many skills don’t translate into market value.
  • We don’t have time or interest to read every loan detail. These details are purposely confusing and it’s hard to determine how expensive our debt is.
  • Most of us are bad at dealing with money and choose to ignore it as a way of coping.
  • For loan servicers, clarity in advice means less profit, which means bad advice is given to their customers.
  • Loan servicers have little reason to invest in better user experiences for their customers.

Now What?

In my case, the 5 Whys exercise created more questions than it answered. However, I’ve developed cleaner statements to test in the market. That’s what I needed!

Next week, I’ll be discussing how I attempted to invalidate these assumptions using a series of “micro MVPs”.

Throw in your email if you’re interested in getting notified about future posts!